Asymmetric Redox-Annulation of Cyclic Amines. Supporting Information

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1 Asymmetric Redox-Annulation of Cyclic Amines YoungKu Kang, Weijie Chen, Martin Breugst,, * and Daniel Seidel, * Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854,United States Department für Chemie, Universität zu Köln, Greinstraße 4, Köln, Germany Table of Contents Part I: Computational Studies Supporting Information 1. Computational Details..S-2 2. Graphical Representations of the Calculated Transition States...S-3 3. Schematic Overview of All Calculated Pathways...S-4 4. Coordinates and Calculated Energies for the Starting Materials.....S-5 5. Coordinates and Calculated Energies for the Products. S-7 6. Coordinates and Calculated Energies for the Intermediates and Transition States of the Uncatalyzed Reaction......S Coordinates and Calculated Energies for the Intermediates and Transition States of the Catalyzed Reaction. S References. S-31 Part II: Experimental Part Additional Experiments Regarding the Regioselectivity of the Asymmetric Redox- Annulation.... S-32 Crystal Structures for Compounds 6c, 7c and 8c....S-33 2D-NMR Analysis S-36 HPLC Profiles. S-40 Copies of NMR Spectra..... S-47 S 1

2 Part I: Computational Studies 1 Computational Details For the computational investigations, the conformational space for each structure was explored using the OPLS-2005 force field 1 and a modified Monte Carlo search algorithm implemented in MacroModel An energy cut-off of 20 kcal mol 1 was employed for the conformational analysis, and structures with heavy-atom root-mean-square deviations (RMSD) less than 2 Å after the initial force field optimizations were considered to be the same conformer. The remaining structures were subsequently optimized with the dispersion-corrected M06-L functional 3 with Grimme s dispersion-correction D3 4 and the double- basis set 6-31+G(d,p). Solvation by toluene was taken into account by using the integral equation formalism polarizable continuum model (IEFPCM) 5 for all calculations. Vibrational analysis verified that each structure was a minimum or transition state. Following the intrinsic reaction coordinates (IRC) confirmed that all transition states connected the corresponding reactants and products on the potential energy surface. Thermal corrections were obtained from unscaled harmonic vibrational frequencies at the same level of theory for a standard state of 1 mol L 1 and K. Entropic contributions to the reported free energies were derived from partition functions evaluated with the quasiharmonic approximation by Truhlar and coworkers. 6 Electronic energies were subsequently obtained from single point calculations of the M06-L-D3 geometries employing the metahybrid M06-2X functional, 7 Grimme s dispersion-correction D3 (zero-damping), the large quadruple- basis set def2-qzvp, 8 and IEFPCM for toluene, a level expected to give accurate energies. 9 An ultrafine grid was used throughout this study for numerical integration of the density. All density functional theory calculations were performed with Gaussian S 2

3 2 Graphical Representations of the Calculated Transition States TS01a TS01b TS TS03 TS04 TS TS06 TS07 TS Figure S1. Graphical representation of the calculated transition states and selected bond lengths [in Å, M06-2X-D3/def2-QZVP/IEFPCM//M06-L-D3/6-31+G(d,p)/IEFPCM(toluene)]. TS09 S 3

4 3 Schematic Overview of All Calculated Pathways H O 2 N N 11, , 11.3 O Iminium Acetates + NH H NO 2 THIQ N N R R N R' N NO 2 OH H 2 O 20, 0.4 H 2 O TS01a N N + HOAc NO 2 TS02 H 2 O TS 21a, b, HOAc HOAc N NO 2 + H 2 O barrierless OAc N barrierless 23, +4.4 N NO 2 O NO 2 2 N TS 22a, b, HOAc N TS TS NO 2 TS01b OH TS HOAc H 2 O TS N OAc 25, H NO 2 TS04 NO TS N OAc 24, 1.2 TS N 26, NO 2 O 2 N TS TS N TS N OAc 27, 2.4 N NO 2 TS08, OAc H 28, NO 2 TS H N 13, , 13.0 NO 2 Scheme S1. Overview about the most important pathways analyzed in redox-annulation reactions [in kcal mol 1, M06-2X-D3/def2-QZVP/IEFPCM//M06-L-D3/6-31+G(d,p)/IEFPCM(toluene)]. S 4

5 4 Coordinates and Calculated Energies for the Starting Materials 4.1 Tetrahydroisoquinoline (THIQ) SCF energy: Zero-point correction: Enthalpy correction: Free energy correction: Quasiharmonic free energy correction: hartree hartree hartree hartree hartree Cartesian Coordinates C C C C C C C C H H N H H C H H H H H H H Nitrobutyraldehyde (10) SCF energy: Zero-point correction: Enthalpy correction: Free energy correction: Quasiharmonic free energy correction: Cartesian Coordinates C O C C H H C H H N H hartree hartree hartree hartree hartree S 5

6 H O O H Acetic Acid SCF energy: Zero-point correction: Enthalpy correction: Free energy correction: Quasiharmonic free energy correction: hartree hartree hartree hartree hartree Cartesian Coordinates C C H H H O O H Water SCF energy: Zero-point correction: Enthalpy correction: Free energy correction: Quasiharmonic free energy correction: hartree hartree hartree hartree hartree Cartesian Coordinates O H H S 6

7 5 Coordinates and Calculated Energies for the Products 5.1 Product 11 SCF energy: Zero-point correction: Enthalpy correction: Free energy correction: Quasiharmonic free energy correction: hartree hartree hartree hartree hartree Cartesian Coordinates C C C C C C C C H H N C H H H H C C C H H C H H N O O H H H H H H Product 12 SCF energy: Zero-point correction: Enthalpy correction: Free energy correction: Quasiharmonic free energy correction: hartree hartree hartree hartree hartree S 7

8 Cartesian Coordinates C C C C C C C C H H N C H H H H C C C H H C H H N O O H H H H H H Product 13 SCF energy: Zero-point correction: Enthalpy correction: Free energy correction: Quasiharmonic free energy correction: Cartesian Coordinates C C C C C C C C H H N hartree hartree hartree hartree hartree S 8

9 C H H H H C C C H H C H H N O O H H H H H H Product 14 SCF energy: Zero-point correction: Enthalpy correction: Free energy correction: Quasiharmonic free energy correction: Cartesian Coordinates C C C C C C C C H H N C H H H H C C C H H C H hartree hartree hartree hartree hartree S 9

10 H N O O H H H H H H S 10

11 6 Coordinates and Calculated Energies for the Intermediates and Transition States of the Uncatalyzed Reaction 6.1 Hemiaminal 20 SCF energy: Zero-point correction: Enthalpy correction: Free energy correction: Quasiharmonic free energy correction: hartree hartree hartree hartree hartree Cartesian Coordinates C C C C C C C C H H N H H C H H H H H H C C H O C H H C H H N H H H O O Azomethine Ylide 21a SCF energy: Zero-point correction: hartree hartree S 11

12 Enthalpy correction: Free energy correction: Quasiharmonic free energy correction: hartree hartree hartree Cartesian Coordinates C C C C C C C C H H N H H C H H H H C C C H H C H H N H H O O H H Azomethine Ylide 21b SCF energy: Zero-point correction: Enthalpy correction: Free energy correction: Quasiharmonic free energy correction: hartree hartree hartree hartree hartree Cartesian Coordinates C C C C C S 12

13 C C C H H N C H H H H C C C H H C H H N H H O O H H H H Transition State TS01a SCF energy: hartree Zero-point correction: hartree Enthalpy correction: hartree Free energy correction: hartree Quasiharmonic free energy correction: hartree Imaginary Frequency: icm 1 Cartesian Coordinates C C C C C C C C H H N H H C H S 13

14 H H H C C C H H C H H N H H O O H H Transition State TS01b SCF energy: hartree Zero-point correction: hartree Enthalpy correction: hartree Free energy correction: hartree Quasiharmonic free energy correction: hartree Imaginary Frequency: icm 1 Cartesian Coordinates C C C C C C C C H H N C H H H H C C C H H C H H N S 14

15 H H O O H H H H Zwitterion 22a SCF energy: Zero-point correction: Enthalpy correction: Free energy correction: Quasiharmonic free energy correction: hartree hartree hartree hartree hartree Cartesian Coordinates C C C C C C C C H H N C H H H H C C C H H C H H N O O H H H H H H S 15

16 6.7 Zwitterion 22b SCF energy: Zero-point correction: Enthalpy correction: Free energy correction: Quasiharmonic free energy correction: hartree hartree hartree hartree hartree Cartesian Coordinates C C C C C C C C H H N C H H H H C C C H H C H H N O O H H H H H H S 16

17 7 Coordinates and Calculated Energies for the Intermediates and Transition States of the Catalyzed Reaction 7.1 Acetylated Hemiaminal 23 SCF energy: Zero-point correction: Enthalpy correction: Free energy correction: Quasiharmonic free energy correction: Cartesian Coordinates C C C C C C C C H H N H H C H H H H H H C C H O C H H C H H N H H C O O C H H H O hartree hartree hartree hartree hartree S 17

18 7.2 Transition State TS02 SCF energy: hartree Zero-point correction: hartree Enthalpy correction: hartree Free energy correction: hartree Quasiharmonic free energy correction: hartree Imaginary Frequency: icm 1 Cartesian Coordinates C C C C C C C C H H N H H C H H H H H H C C H O C H H C H H N H H C O O C H H H O S 18

19 7.3 Transition State 03 SCF energy: hartree Zero-point correction: hartree Enthalpy correction: hartree Free energy correction: hartree Quasiharmonic free energy correction: hartree Imaginary Frequency: icm 1 Cartesian Coordinates C C C C C C C C H H N H H C H H H H C C O C H H C H H N H H O O H H H C C H H H O S 19

20 7.4 Acetylated Hemiaminal 24 SCF energy: Zero-point correction: Enthalpy correction: Free energy correction: Quasiharmonic free energy correction: hartree hartree hartree hartree hartree Cartesian Coordinates C C C C C C C C H H N H H C H H H H C C O C H H C H H N H H O O H H H C C H H H O S 20

21 7.5 Transition State TS04 SCF energy: hartree Zero-point correction: hartree Enthalpy correction: hartree Free energy correction: hartree Quasiharmonic free energy correction: hartree Imaginary Frequency: icm 1 Cartesian Coordinates C C C C N C C C H H C H H C H H N H O O C C C C H H H H H H H H O H C C H H H O H S 21

22 7.6 Ammonium Nitronate 25 SCF energy: Zero-point correction: Enthalpy correction: Free energy correction: Quasiharmonic free energy correction: hartree hartree hartree hartree hartree Cartesian Coordinates C C C C N C C C H H C H H C H H N H O O C C C C H H H H H H H H O H C C H H H O H S 22

23 7.7 Transition State TS05 SCF energy: hartree Zero-point correction: hartree Enthalpy correction: hartree Free energy correction: hartree Quasiharmonic free energy correction: hartree Imaginary Frequency: icm 1 Cartesian Coordinates C C C C N C C C H H C H H C H H N H O O C C C C H H H H H H H H O H C C H H H O H S 23

24 7.8 Transition State TS06 SCF energy: hartree Zero-point correction: hartree Enthalpy correction: hartree Free energy correction: hartree Quasiharmonic free energy correction: hartree Imaginary Frequency: icm 1 Cartesian Coordinates C C C C C C C C H H N H H C H H H H C C O C H H C H H N H H O O H H H C C H H H O S 24

25 7.9 Azomethine Ylide 26 SCF energy: Zero-point correction: Enthalpy correction: Free energy correction: Quasiharmonic free energy correction: hartree hartree hartree hartree hartree Cartesian Coordinates C C C C C C C C H H N C H H H H C C C H H C H H N H H O O H H H H Transition State TS07 SCF energy: Zero-point correction: Enthalpy correction: Free energy correction: Quasiharmonic free energy correction: hartree hartree hartree hartree hartree S 25

26 Imaginary Frequency: icm 1 Cartesian Coordinates C C C C N C C C H H C H H C H H N O O C C C C H H H H H H O C C H H H O H H H H H Acetylated Hemiaminal 27 SCF energy: Zero-point correction: Enthalpy correction: Free energy correction: Quasiharmonic free energy correction: hartree hartree hartree hartree hartree S 26

27 Cartesian Coordinates C C C C N C C C H H C H H C H H N O O C C C C H H H H H H O C C H H H O H H H H H Transition State TS08 SCF energy: hartree Zero-point correction: hartree Enthalpy correction: hartree Free energy correction: hartree Quasiharmonic free energy correction: hartree Imaginary Frequency: icm 1 S 27

28 Cartesian Coordinates C C C C N C C C H H C H H C H H N H O O C C C C H H H H H H O C C H H H O H H H H Ammonium Nitronate 28 SCF energy: Zero-point correction: Enthalpy correction: Free energy correction: Quasiharmonic free energy correction: hartree hartree hartree hartree hartree S 28

29 Cartesian Coordinates C C C C N C C C H H C H H C H H N H O O C C C C H H H H H H O C C H H H O H H H H Transition State TS09 SCF energy: hartree Zero-point correction: hartree Enthalpy correction: hartree Free energy correction: hartree Quasiharmonic free energy correction: hartree Imaginary Frequency: 81.6 icm 1 S 29

30 Cartesian Coordinates C C C C N C C C H H C H H C H H N H O O C C C C H H H H H H O C C H H H O H H H H S 30

31 8 References 1 Banks, J. L.; Beard, H. S.; Cao, Y.; Cho, A. E.; Damm, W.; Farid, R.; Felts, A. K.; Halgren, T. A.; Mainz, D. T.; Maple, J. R.; Murphy, R.; Philipp, D. M.; Repasky, M. P.; Zhang, L. Y.; Berne, B. J.; Friesner, R. A.; Gallicchio, E.; Levy, R. M. J. Comput. Chem. 2005, 26, MacroModel, V. 10.6, Schrödinger, LLC, New York, NY, Zhao, Y.; Truhlar, D. G. J. Chem. Phys. 2006, 125, Grimme, S.; Antony, J.; Ehrlich, S.; Krieg, H. J. Chem. Phys. 2010, 132, Cancès, E.; Mennucci, B.; Tomasi, J. J. Chem. Phys. 1997, 107, Ribeiro, R. F.; Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. B 2011, 115, Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, Weigend, F.; Ahlrichs, R. Phys. Chem. Chem. Phys. 2005, 7, Goerigk, L.; Grimme, S. Phys. Chem. Chem. Phys. 2011, 13, Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian, Inc., Wallingford CT, S 31

32 Part II: Experimental Part Table S1. Additional experiments regarding the regioselectivity of the asymmetric redoxannulation. entry acid (equiv) solvent ratio of 6a/7a and 8a/9a c yield of 6a/7a (%) b yield of 8a/9a (%) b dr of 8a/9a c 1 AcOH (10) toluene 5: :1 2 2-EHA (10) toluene 1:1.4 ND 40 1:1 3 2-EHA (5) toluene 1:2.4 ND 41 1:1 4 2-EHA (2.5) toluene 1:1.5 ND ND 1.4:1 5 2-EHA (5) xylenes 1:8.5 ND :1 6 2-EHA (10) xylenes 1:8.6 ND :1 7 a 2-EHA (10) xylenes 1.2:1 ND ND 1:1 a Addition of aldehyde over 2 min. b Isolated yield of both diastereomers. c Regioisomeric and diastereomeric ratios were determined by 1 H NMR of crude reaction mixtures. ND: not determined. S 32

33 Crystal Structure for Compound 6c Compound 6c was recrystallized from methanol and dichloromethane. The ellipsoid contour probability level for the thermal ellipsoid plot is 50%. S 33

34 Crystal Structure for Compound 7c Compound 7c was recrystallized from dichloromethane and pentane. The ellipsoid contour probability level for the thermal ellipsoid plot is 50%. S 34

35 Crystal Structure for Compound 8c Compound 8c was recrystallized from dichloromethane and pentane. The ellipsoid contour probability level for the thermal ellipsoid plot is 50%. S 35

36 2D-NMR Analysis for Compound 6a, Selected Interactions 1 H NMR shifts Proton Chemical shift H H H H H 5, H Me D-NMR Analysis for Compound 7a, Selected Interactions 1 H NMR shifts Proton Chemical shift H H H H H H Me 0.95 S 36

37 2D-NMR Analysis for Compound 6k, Selected Interactions 1 H NMR shifts Proton Chemical shift H H H H H H 6,H D-NMR Analysis for Compound 8a, Selected Interactions 1 H NMR shifts Proton Chemical shift H 1, H 3, H 5, H H H Me 0.78 S 37

38 2D-NMR Analysis for Compound 9a, Selected Interactions 1 H NMR shifts Proton Chemical shift H H H H H H Me D-NMR Analysis for Compound 8k, Selected Interactions 1 H NMR shifts Proton Chemical shift H H H H 4, H H H S 38

39 2D-NMR Analysis for Compound 11, Selected Interactions 1 H NMR shifts Proton Chemical shift H H H 3, H H H H 7, H S 39

40 HPLC Profile of 5a S 40

41 HPLC Profile of 6a S 41

42 HPLC Profile of 7a S 42

43 HPLC Profile of 5k (Product was reduced to the corresponding alcohol using NaBH 4 for HPLC analysis) S 43

44 HPLC Profile of 6k S 44

45 HPLC Profile of 16 S 45

46 HPLC Profile of 18 S 46

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