SUPPORTING INFORMATION. Stereomutation of Conformational Enantiomers of 9-Isopropyl-9-formyl fluorene and Related Acyl Derivatives.
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1 SUPPORTING INFORMATION Stereomutation of Conformational Enantiomers of 9-Isopropyl-9-formyl fluorene and Related Acyl Derivatives. Daniele Casarini*, Lodovico Lunazzi, and Andrea Mazzanti* Department of Chemistry, University of Basilicata, via N. Sauro 85, Potenza 85100, Italy, and Department of Organic Chemistry A. Mangini, University of Bologna, Viale Risorgimento 4, Bologna 40136, Italy INDEX: - Figure S1: 1 H Variable Temperature spectra of compound 1 (Me signal) (Page S2) - Figure S2: 1 H Variable Temperature spectra of compound 1 (H-1,8 signal) (Page S3) - Figure S3: 1 H Variable Temperature spectra of compound 2 (Page S4) - Figure S4: 13 C Variable Temperature spectra of compound 3 (Page S5) - Figure S5: MM-calculated PES of compound 3 (Page S6) - X-ray data for compound 3 (Page S7) - Synthetic procedure for the preparation of 1-3 and their intermediates (Pages S8-S10) - 1 H and 13 C NMR spectra of 1-3 and intermediates (Pages S11-S15) - HPLC analytical traces of 1-3 (Pages S16-S18) - Table S1: DFT computational data of 1-3 (Page S19) - Table S2: DFT computational data of 1-3 (Enthalpy) (Page S20) - Table S3: DFT computational data of 1-3 (Free energy) (Page S21) - Computational details of 1-3 (Pages S22-S36) S1
2 CHO T ( C) k(s -1 1 ) ppm FIGURE S-1 Temperature dependence (left) of the 1 H methyl signals (600 MHz) of 1 in CHF 2 Cl/CHFCl 2. On the right the simulation obtained with the rate constants reported. S2
3 CHO T ( C) k(s -1 ) 1-55 > ppm FIGURE S-2. Temperature dependence (left) of the H-1,8 aromatic signal (600 MHz) of 1 in CHF 2 Cl/CHFCl 2. On the right the simulation obtained with the rate constants reported. S3
4 COMe T ( C) k(s -1 ) 2-23 > < ppm FIGURE S-3. Temperature dependence of the 1 H isopropyl methyl signals of 2 (600 MHz) in CHF 2 Cl/CHFCl 2. On the right the simulation obtained with the rate constants reported. S4
5 CO-Bu t T ( C) k(s -1 ) 3-23 > < ppm FIGURE S-4. Temperature dependence of the 13 C isopropyl methyl signals of 3 (150.8 MHz) in CHF 2 Cl/CHFCl 2. On the right the simulation obtained with the rate constants reported. S5
6 E C9-CO Rotation C9-iPr Rotation FIGURE S-5. MMX computed energy (in kcal mol -1 ) surface of 3. The black line represents the pathway involving the 360 rotation about the C9-COBu t bond. The red line describes the process for the C9-Pr i bond rotation (also involving the low amplitude libration 15 of the C9-CO bond). The full and hollow circles represent the enantiomeric ground states. The squares represent the transition states reported on the top (obtained by DFT computations). The barrier for the black line pathway is 13.0 (MMX) or 15.5 (DFT) kcal mol -1 and that for the red line 7.5 (MMX) or 8.0 (DFT) kcal mol -1. S6
7 Crystal Data for 1-(9-isopropyl-9H-fluoren-9-yl)-2,2-dimethylpropan-1-one (3) Molecular formula: C 21 H 24 O, M r = , Monoclinic, space group P21/C (No. 14), a = (10), b = (3), c = (19), β = (2) Å, V = (4) Å 3, T = 295(2) K, Z = 4, ρ c = g cm 3, F(000) = 632, graphite-monochromated Mo Kα radiation (λ = Å), μ(mo Kα ) = mm 1, colourless brick ( mm 3 ), empirical absorption correction with SADABS (transmission factors: ), 2400 frames, exposure time 10 s, 1.62 θ 28.65, 10 h 10, 33 k 33, 12 l 12, reflections collected, 4184 independent reflections (R int = ), solution by direct methods (SHELXS97 a 2 ) and subsequent Fourier syntheses, full-matrix least-squares on F o (SHELX97 a ), hydrogen atoms refined with a riding model, data / restraints / parameters = 4184 / 0 / 205, S(F 2 ) = 1.892, R(F) = and wr(f 2 ) = on all data, R(F) = and wr(f 2 ) = for 3395 reflections with I > 2σ(I), weighting scheme w = 1/[σ 2 (F 2 o ) + (0.0663P) P] where P = (F 2 o + 2F 2 c )/3, largest difference peak and hole and e Å 3. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44) ; deposit@ccdc.cam.ac.uk). a) Sheldrick, G. M. SHELX97; Universität Göttingen, Germany, S7
8 Synthetic procedure and intermediates characterization 1) LDA 2) ipr-i -15 C / 2 h O 1) LDA 2) CH 2 O -15 C to +25 C, 2h CrO 3 /H 2 SO 4 OH +25 C / h 1 R-Li -78 C, 2 h HO O R R CrO 3 /H 2 SO C / h R=Me, 2 R=Bu t,3 9-isopropyl-9H-fluorene. To a stirred solution of N,N-diisopropylamine (3.7 ml, 26 mmol in 30 ml of anhydrous THF) kept at 10 C under nitrogen, 15.0 ml (24.0 mmol, 1.6M solution in hexanes) of n-buli were slowly added. The mixture was allowed to react at -10 C for 30 min, then slowly transferred by a double-tipped needle into a solution of 9H-fluorene (3.32 g, 20 mmol in 40 ml of anhydrous THF) kept at -15 C. The resulting yellow solution was stirred at -15 C for additional 20 min, and then a solution of 2-iodopropane (2.2 ml, 22 mmol in 5 ml of dry THF) was added in 10 min. After stirring for additional 30 min the reaction was quenched with 20 ml of H 2 O. The extracted S8
9 organic layer (Et 2 O) was dried (Na 2 SO 4 ) and evaporated, to obtain a slightly yellow oil (3.9 g, yield 93%), containing the title product and a small amount of fluorene (3-5%). Analytically pure sample can be obtained by semipreparative HPLC (C18, Acetonitrile/H 2 O 80:20). 1 H NMR (600 MHz, CD 3 CN, +25 C) δ 0.81 (d, J = 7.0 Hz, 6H), 2.60 (double septet, J = 7.0, 3.4 Hz, 1H), 3.97 (d, J = 3.4 Hz, 1H), 7.32 (td, J = 7.5, 1.2 Hz, 2H), 7.32 (t, J = 7.5 Hz, 2H), 7.59 (dd, J = 7.5, 1.2 Hz, 2H), 7.81 (d, J = 7.5 Hz, 2H). 13 C NMR (150.8 MHz, CD 3 CN, +25 C) δ 19.7 (CH 3 ), 33.3 (CH), 54.8 (CH), (CH), (CH), (CH), (CH), (C q ), (C q ). (9-isopropyl-9H-fluoren-9-yl)methanol. To a stirred solution of N,N-diisopropylamine (1.4 ml, 10 mmol in 10 ml of anhydrous THF) kept at 10 C under nitrogen, 6.0 ml (9.6 mmol, 1.6M solution in hexanes) of n-buli were slowly added. The mixture was allowed to react at -10 C for 30 min, then a solution of 9-isopropyl-9H-fluorene (1.87 g, 9 mmol in 10 ml of anhydrous THF) was added at -15 C. The resulting deeply red solution was stirred at -5 C for additional 30 min, and then solid paraformaldehyde (0.54 g, 18 mmol) was rapidly added under nitrogen flux, and the mixture was warmed to ambient temperature. In 10 to 20 min the red solution changed to yellow, and after 30 min of additiona stirring, it was quenched with 20 ml of H 2 O. The extracted organic layer (Et 2 O) was dried (Na 2 SO 4 ) and evaporated, to obtain a yellow oil. Purification on silica gel (hexanes/etoac 95:5 to 80:20) yelded the title product as a colourless oil (1.85 g, yield 86%). 1 H NMR (600 MHz, CDCl 3, +25 C) δ 0.76 (d, J = 6.9 Hz, 6H), 1.27 (t, J = 6.5 Hz, OH), 2.55 (septet, J = 6.9, Hz, 1H), 3.99 (d, J = 6.5 Hz, 2H), 7.30 (td, J = 7.5, 1.1 Hz, 2H), 7.32 (td, J = 7.4, 1.1 Hz, 2H), 7.49 (d, J = 7.5 Hz, 2H), 7.73 (d, J = 7.4 Hz, 2H). 13 C NMR (150.8 MHz, CDCl 3, +25 C) δ 17.8 (CH 3 ), 32.6 (CH), 60.1 (C q ), 67.4 (CH 2 ), (CH), (CH), (CH), (CH), (C q ), (C q ). S9
10 9-isopropyl-9H-fluorene-9-carbaldehyde. H 2 SO 4 (0.2 ml, 1N solution) was added, at room temperature, to a solution of (9-isopropyl-9H-fluoren-9-yl)methanol (2.0 g, 8.5 mmol in 40 ml of acetone); aliquots of CrO 3 were then added to the mixture, following the reaction by TLC (hexanes/acetone 9:1). When the alcohol disappeared, H 2 O was added and the mixture was evaporated at reduced pressure. The crude was extracted with Et 2 O, the organic layer was separated and dried (Na 2 SO 4 ), and the solvent removed at reduced pressure. The residue was purified on a silica gel column (hexanes/aceton 9:1) to obtain the title compound (1.05g, yield 52%) and 9-fluorenone as byproduct (0.8 g). Analytically pure samples of 1 were obtained by semipreparative HPLC (C18 column, 10 μm, 250x21.2mm, acetonitrile/h 2 O 90:10 v/v). S10
11 S11
12 S12 OH
13 O 1 S13
14 O 2 S14
15 O 3 S15
16 Compound 1 Reported by User: System Project Name: LunaC18 S A M P L E I N F O R M A T I O N Sample Name: Fluorene-CHO-analitica Acquired By: System Vial: 2 Date Acquired: 4/1/2008 9:12:14 AM Injection #: 1 Flow (ml / min) : 5.0 Injection Volume: ul Solvent 1: ACN 80.0 % Run Time: 20.0 Minutes Solvent 2: Water 20.0 % Acq. Method Set: azeo_10_5 Column: Luna C18 Compound Name: compound 1 Channel Name: 2487Channel AU Minutes RT Area % Area Height Report Method: Sample Data Printed 9:09:16 AM 4/15/2008 Page: S-16
17 Compound 2 Reported by User: System Project Name: LunaC18 S A M P L E I N F O R M A T I O N Sample Name: Fluorene-CO-Me-analitica Acquired By: System Vial: 1 Date Acquired: 4/1/2008 9:56:51 AM Injection #: 1 Flow (ml / min) : 5.0 Injection Volume: ul Solvent 1: ACN 80.0 % Run Time: 20.0 Minutes Solvent 2: Water 20.0 % Acq. Method Set: azeo_10_5 Column: Luna C18 Compound Name: compound 2 Channel Name: 2487Channel AU Minutes RT Area % Area Height Report Method: Sample Data Printed 9:10:21 AM 4/15/2008 Page: S-17
18 Compound 3 Reported by User: System Project Name: LunaC18 S A M P L E I N F O R M A T I O N Sample Name: Fluorene-CO-Tbu-analitica Acquired By: System Vial: 1 Date Acquired: 4/1/ :44:05 AM Injection #: 1 Flow (ml / min) : 5.0 Injection Volume: ul Solvent 1: ACN 90.0 % Run Time: 25.0 Minutes Solvent 2: Water 10.0 % Acq. Method Set: azeo_0_5 Column: Luna C18 Compound Name: Compound 3 Channel Name: 2487Channel AU Minutes RT Area % Area Height Report Method: Sample Data Printed 9:11:14 AM 4/15/2008 Page: S-18
19 Table S1: calculated electronic energies Method/ basis set Total Energy (a.u.) Rel. E. (kcal/mol) img. Freq. Compound 1 Ground state B3LYP/6-31G(d) Ground State n 2 B3LYP/6-31G(d) TS ipr rotation TS-1 B3LYP/6-31G(d) TS ipr rotation TS-2 B3LYP/6-31G(d) TS C9-CHO rotation B3LYP/6-31G(d) Compound 2 Ground State B3LYP/6-31G(d) TS ipr rotation TS-1 B3LYP/6-31G(d) TS ipr rotation TS-2 B3LYP/6-31G(d) TS C9-COMe rotation B3LYP/6-31G(d) Compound 3 Ground State B3LYP/6-31G(d) TS ipr rotation TS-1 B3LYP/6-31G(d) TS ipr rotation TS-2 B3LYP/6-31G(d) TS C9-COtBu rotation B3LYP/6-31G(d) TS CO-tBu rotation B3LYP/6-31G(d) S19
20 Tables S2: Sum of electronic and thermal Enthalpies data Method/ basis set Energy (a.u.) Rel. H. (kcal/mol) img. Freq. Compound 1 Ground state B3LYP/6-31G(d) -732, ,000 0 Ground state n 2 B3LYP/6-31G(d) -732, ,670 0 TS ipr rotation TS-1 B3LYP/6-31G(d) -732, ,531 1 TS ipr rotation TS-2 B3LYP/6-31G(d) -732, ,089 1 TS C9-CHO rotation B3LYP/6-31G(d) -732, ,211 1 Compound 2 Ground State B3LYP/6-31G(d) -771, ,000 0 TS ipr rotation TS-1 B3LYP/6-31G(d) -771, ,330 1 TS ipr rotation TS-2 B3LYP/6-31G(d) -771, ,362 1 TS C9-COMe rotation B3LYP/6-31G(d) -771, ,330 1 Compound 3 Ground State B3LYP/6-31G(d) -889, ,000 0 TS ipr rotation TS-1 B3LYP/6-31G(d) -889, ,483 1 TS ipr rotation TS-2 B3LYP/6-31G(d) -889, ,073 1 TS C9-COtBu rotation B3LYP/6-31G(d) -889, ,842 1 TS CO-tBu rotation B3LYP/6-31G(d) -889, ,698 1 S20
21 Tables S2: Sum of electronic and thermal Free Energies data Compound 1 Method/ basis set Total Energy (a.u.) Rel. Free Energies (kcal/mol) img. Freq. Ground state B3LYP/6-31G(d) -732, ,000 0 Ground state n 2 B3LYP/6-31G(d) -732, ,428 0 TS ipr rotation TS-1 B3LYP/6-31G(d) -732, ,868 1 TS ipr rotation TS-2 B3LYP/6-31G(d) -732, ,082 1 TS C9-CHO rotation B3LYP/6-31G(d) -732, ,079 1 Compound 2 Ground State B3LYP/6-31G(d) -771, ,000 0 TS ipr rotation TS-1 B3LYP/6-31G(d) -771, ,665 1 TS ipr rotation TS-2 B3LYP/6-31G(d) -771, ,020 1 TS C9-COMe rotation B3LYP/6-31G(d) -771, ,809 1 Compound 3 Ground State B3LYP/6-31G(d) -889, ,000 0 TS ipr rotation TS-1 B3LYP/6-31G(d) -889, ,651 1 TS ipr rotation TS-2 B3LYP/6-31G(d) -889, ,098 1 TS C9-COtBu rotation B3LYP/6-31G(d) -889, ,549 1 TS CO-tBu rotation B3LYP/6-31G(d) -889, ,027 1 S21
22 Compound 1 Ground State Method: B3LYP/6-31G(d) SCF Done: E(RB+HF-LYP) = A.U. after 7 cycles Imaginary frequencies: 0 (61.9) Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= Input orientation: Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z S22
23 Compound 1 Ground State n 2 Method: B3LYP/6-31G(d) SCF Done: E(RB+HF-LYP) = A.U. after 8 cycles Imaginary frequencies: 0 (48.8) Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= Input orientation: Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z S23
24 Compound 1 Transition State ipr rotation (TS-1) Method: B3LYP/6-31G(d) SCF Done: E(RB+HF-LYP) = A.U. after 10 cycles Imaginary frequencies: 1 (-77.9) Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= Input orientation: Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z S24
25 Compound 1 Transition State ipr rotation (TS-2) Method: B3LYP/6-31G(d) SCF Done: E(RB+HF-LYP) = A.U. after 8 cycles Imaginary frequencies: 1 (-65.6) Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= Input orientation: Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z S25
26 Compound 1 Transition State CHO rotation Method: B3LYP/6-31G(d) SCF Done: E(RB+HF-LYP) = A.U. after 8 cycles Imaginary frequencies: 1 (-117.8) Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= Input orientation: Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z S26
27 Compound 2 Ground State Method: B3LYP/6-31G(d) SCF Done: E(RB+HF-LYP) = A.U. after 8 cycles Imaginary frequencies: 0 (53.5) Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= Input orientation: Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z S27
28 Compound 2 Transition State ipr rotation (TS-1) Method: B3LYP/6-31G(d) SCF Done: E(RB+HF-LYP) = A.U. after 8 cycles Imaginary frequencies: 1 (-79.1) Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= Input orientation: Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z S28
29 Compound 2 Transition State ipr rotation (TS-2) Method: B3LYP/6-31G(d) SCF Done: E(RB+HF-LYP) = A.U. after 7 cycles Imaginary frequencies: 1 (-63.8) Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= Input orientation: Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z S29
30 Compound 2 Transition State COMe rotation Method: B3LYP/6-31G(d) SCF Done: E(RB+HF-LYP) = A.U. after 8 cycles Imaginary frequencies: 1 (-24.2) Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= Input orientation: Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z S30
31 Compound 3 Ground State Method: B3LYP/6-31G(d) SCF Done: E(RB+HF-LYP) = A.U. after 10 cycles Imaginary frequencies: 0 (20.7) Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= Input orientation: Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z S31
32 Compound 3 Transition State ipr rotation (TS-1) Method: B3LYP/6-31G(d) SCF Done: E(RB+HF-LYP) = A.U. after 15 cycles Imaginary frequencies: 1 (-85.7) Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= Input orientation: Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z S32
33 Compound 2 Transition State ipr rotation (TS-2) Method: B3LYP/6-31G(d) SCF Done: E(RB+HF-LYP) = A.U. after 8 cycles Imaginary frequencies: 1 (-67.9) Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= Input orientation: Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z S33
34 Compound 3 Transition State C9-COtBu rotation Method: B3LYP/6-31G(d) SCF Done: E(RB+HF-LYP) = A.U. after 8 cycles Imaginary frequencies: 1 (-61.9) Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= Input orientation: Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z S34
35 Compound 3 Transition State CO-tBu rotation Method: B3LYP/6-31G(d) SCF Done: E(RB+HF-LYP) = A.U. after 7 cycles Imaginary frequencies: 1 (-23.0) Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= S35
36 Input orientation: Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z S36
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