DBU-mediated Diastereoselective Aldol-type Cyanomethylation of Isatins
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1 DBU-mediated Diastereoselective Aldol-type Cyanomethylation of Isatins V. U. Bhaskara Rao, Krishna Kumar, Tamal Das, Kumar Vanka and Ravi P. Singh * Department of Chemistry, Indian Institute of Technology, Delhi, Hauz Khas, New Delhi , India. Physical Chemistry Division, National Chemical Laboratory, Dr. Homi Bhabha Road, Pune , India Supporting Information Content of supporting information 1. General reaction procedure for Cyanomethylation Reaction S2 2. Time dependent changes in dr during reaction progress....s3 3. Kinetically controlled product vs thermodynamically controlled product S4 4. Crystal Structure...S5 5. Copies of 1 H- 13 C NMR.S6 6. Details of DFT calculations.s30 7. References S30 S1
2 1. General reaction procedure for Cyanomethylation Reaction. To a solution of N-protected isatin 1 (0.1 mmol) in solvent (specified below) (1 ml) was added Phenyl acetonitrile (0.12 mmol) at room temperature under N 2. The resulting mixture was stirred for 1 min at the same temperature and then DBU (0.18 mmol) was added drop wise. The resulting mixture was stirred for 2.25h at room temperature. The progress of the reaction was monitored by thin layer chromatography. Once the reaction completed it was quenched by addition of 1M HCl (1.0 ml) solution. The resulting mixture was extracted with ethyl acetate (5 ml 3). The combined organic layers were dried over Na 2 SO 4, filtered, and concentrated under reduced pressure to provide an oily residue that was purified by flash chromatography on silica gel (eluent: EtOAc/PE = 1/3, v/v). The ratio of diastereomers was determined by 1 H NMR. Materials: Phenyl acetonitrile 2a-2g was purchased from Sigma-aldrich and used without further purification. N-protected Isatins 1a-1o were prepared according to known literature procedures. 1 R O N P 1A, R=H,P=-CH 3 1B, R=H,P=-CH 2 Ph 1C, R=H,P=-CH 2 -(4OMe-C 6 H 4 ) 1D, R=H,P=-C(Ph) 3 1E, R=5-Me,P=-C(Ph) 3 1F, R=5-Cl,P=-C(Ph) 3 1G, R=5-Br,P=-C(Ph) 3 1H, R=5-NO 2,P=-C(Ph) 3 O 1I, R=5-OCF 3,P=-C(Ph) 3 1J, R=5-Ph,P=-C(Ph) 3 1K, R=4-Cl,P=-C(Ph) 3 1L, R=4-Br,P=-C(Ph) 3 1M, R=6-Cl,P=-C(Ph) 3 1N, R=6-Br,P=-C(Ph) 3 1O, R=7-F,P=-C(Ph) 3 1P,R=5-F,P=-C(Ph) 3 R CN 2a,R=4-H, 2b,R=4-CH 3, 2c,R=4-OCH 3, 2d,R=4-Cl, 2e,R=4-CF 3, 2g,R=3,5-bisCF 3. 2f CN S-Figure 1: The Structure of N- Protected Isatins 1 and Phenyl acetonitrile 2 S2
3 2. Time dependent changes in dr during reaction progress: The time-dependent dr changes of the product during the reaction progress was observed and the reaction was anti-selective at very early stage. dr > Time > Table S1: Time dependent changes in dr during reaction S3
4 3. Kinetically controlled product vs thermodynamically controlled product: The product with low dr were treated under the optimized DBU-catalyzed reaction conditions. However, we did not observe any change in the dr, suggesting that the reaction may be kinetically controlled leading to an anti-adduct. Reference: 1. (a) Jung, H. H.; Buesking, A. W.; Ellman, J. A. Org. Lett., 2011, 13, (b) Chen, D.; Xu, M. H. Chem. Commun. 2013, 49, S4
5 4. Crystal Structure: Figure S2. (a) Molecular structure of compound 3d. Thermal ellipsoids are drawn at the 30% probability level. All the hydrogen atoms are omitted for clarity. S5
6 5. Copies of 1 H- 13 C NMR 1H.esp c.esp S6
7 C.esp S7
8 C.esp S8
9 1H.esp C.esp S9
10 1H.esp O 2 N HO Ph CN O N Tr 3h C.esp S10
11 1H.esp C.esp S11
12 cd r.esp C.esp S12
13 1H.esp Cl HO Ph CN N Tr 3k O C.esp S13
14 1H.esp C.esp S14
15 1H.esp C.esp S15
16 1H.esp C.esp S16
17 1H.esp C.esp S17
18 1H.esp C.esp S18
19 1H.esp C.esp S19
20 1H.esp C.esp S20
21 1H.esp C.esp S21
22 1H.esp C.esp S22
23 1H.esp C.esp S23
24 1H.esp F 3 C F HO N 4g Tr CN O C.esp S24
25 1H.esp C.esp S25
26 1H.esp C.esp S26
27 1H.esp C.esp S27
28 1H.esp C.esp S28
29 Ph HO N N CH 3 6 CH 3 13C.esp S29
30 6. Details of DFT calculations All the calculations in this study have been performed with density functional theory (DFT), with the aid of the Turbomole 6.4 suite of programs, 1 using the PBE functional. 2 The TZVP 3 basis set has been employed. The resolution of identity (RI), 4 along with the multipole accelerated resolution of identity (marij) 5 approximations have been employed for an accurate and efficient treatment of the electronic Coulomb term in the DFT calculations. Solvent correction were incorporated with optimization calculations using the COSMO model, 6 with diethyl ether (ε = 4.33) as the solvent. The values reported are G values, with zero point energy corrections, internal energy and entropic contributions included through frequency calculations on the optimized minima with the temperature taken to be K. Harmonic frequency calculations were performed for all stationary points to confirm them as a local minima or transition state structures. 7. References: (1) Ahlrichs, R.; Bar, M.; Ha ser, M.; Horn, H.; Kolmel, C. Chem. Phys. Lett. 1989, 162, (2) Perdew, J. P.; Burke, K.; Ernzerhof, M. Phys. Rev. Lett. 1996, 77, (3) Ansgar, S.; Christian, H.; Reinhart, A. J. Chem. Phys. 1994, 100, (4) Eichkorn, K.; Treutler, O.; Ö hm, H.; Haser, M.; Ahlrichs, R. Chem. Phys. Lett. 1995, 240, (5) Sierka, M.; Hogekamp, A.; Ahlrichs, R. J. Chem. Phys. 2003, 118, (6) Klamt, A.; Schuurmann, G. J. Chem. Soc., Perkin Trans , S30
31 PBE/TZVP optimized geometries for all the compounds and transition states Syn-TS anti-ts Figure S3. The transition state structures of both the syn and anti cases I (RC) C C C C C C C C H H H H N O O C C C C S31
32 C H C H C H H H C C C C H C H C H H H C C C C H C H C H H H C C C C C C H H H H H C H H C N S32
33 C C C C C C H H H H H C H C N N H H C H H H H H H H H II-TS H H C H C H H C H H C H H N C N S33
34 H C H N C C H H C H H H C C H H C C C C C C C O H H H H C N O H H C C C H C C C C C C C C H S34
35 H H H C C H C H C C H H C C C C H H H C C C C H H H H H H C III-intermediate C C C C C C C C C C C C S35
36 C N C C C C C C C C O O C C C C C C N C C C C C C C C N C N C C C C C C C C H H H H H H H H S36
37 H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H IV-syn intermediate C N C C C N C C S37
38 C C C O C C N C C C C C C C C C C C C C O C C C C C C C C C C C C C C N C C C C C C H H H H S38
39 H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H V-syn TS C C C C C S39
40 C C C N C C C N C C C C C O C C C C C C C O C C C C C C C C C C C C N C C C N C C C C C C H S40
41 H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H S41
42 VI syn product C C C C C C C C N C C C N C C C C C O C C C C C C C O C C C C C C C C C C C C N C C C N S42
43 C C C C C C H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H S43
44 H H VII-anti itermediate C N C C C N C C C C C O C C N C C C C C C C C C C C C C O C C C C C C C C C C C S44
45 C C C N C C C C C C H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H S45
46 H H H H H H VIII-anti TS C N H O C C C C C H C C H H C H H C H C C H H N C H H C H H H C C H H H C S46
47 H C C H H H C H C C C C N C O H C H C C C C C H C H C C C C C C H H H C C H C H C H C H C N S47
48 H H H H H H H H H IX anti product C C C C N C C C C C O C C C C C C C O C C C C C C C C C C C C N C C S48
49 C N C C C C C C H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H C S49
50 C C C H C H C H H H C N S50
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