Asymmetric reduction of 2-bromo-1-phenylethylidenemalononitrile with chiral NAD(P)H models

Tetrahedron Asymmetry

Volumn 10, Issue 22, 1999, Pages 4343-4347

  Li, Jing ^a   Liu, You Cheng ^a,c   Deng, Jin Gen ^b  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

^b CHENGDU INSTITUTE OF ORGANIC CHEMISTRY   (China)

^c LANZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

2 BROMO 1 PHENYLETHYLIDENEMALONONITRILE; CYANIDE; CYCLOPROPANE; DIHYDROPYRIDINE DERIVATIVE; MALONONITRILE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHIRALITY; ENANTIOMER; PRIORITY JOURNAL;

EID: 0033387044     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00481-4     Document Type: Article

References (21)

1. Ohnishi, Y.; Kagami, M.; Ohno, A. J. Am. Chem. Soc. 1975, 97, 4766-4768.
2. (a) Inouye, Y.; Oda, J.; Baba, N. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1983; Vol. 2, pp. 91-124;
3. (b) Burgess, V. A.; Davies, S. G.; Skerlj, R. T. Tetrahedron: Asymmetry 1991, 2, 299-328 and references cited therein.
4. (a) Ohno, A.; Ikeguchi, M.; Kimura, T.; Oka, S. J. Am. Chem. Soc. 1979, 101, 7036-7040;
5. (b) Obika, S.; Nishiyama, T.; Tatematsu, S.; Miyashita, K.; Iwata, C.; Imanishi, T. Tetrahedron 1997, 53, 593-602;
6. (c) Burgess, V. A.; Davies, S. G.; Skerlj, R. T. J. Chem. Soc., Chem. Commun. 1990, 1759-1762;
7. (d) De Vries, J. G.; Kellogg, R. M. J. Am. Chem. Soc. 1979, 101, 2759-2761;
8. (e) Seki, M.; Baba, N.; Oda, J.; Inouye, Y. J. Am. Chem. Soc. 1981, 103, 4613-4615.
9. (a) Liu, Y. C.; Li, B.; Guo, Q. X. Tetrahedron Lett. 1994, 35, 8429-8432;
10. (b) Liu, Y. C.; Li, B.; Guo, Q. X. Tetrahedron 1995, 51, 9671-9680.
11. Imanishi, T.; Bbika, S.; Nishiyama, T.; Nishimoto, M.; Hamano, Y.; Miyashita, K.; Iwata, C. Chem. Pharm. Bull. 1996, 44, 267-272.
12. Yankee, E. W.; Spencer, B.; Howe, N. E.; Cram, D. J. J. Am. Chem. Soc. 1973, 94, 4220-4230.
13. 3CN. The product 3 with reversed configuration could be formed through 180° rotation of the benzyl group about its bond to the methylene and recyclization to the cyclopropane ring. Based on the above equilibrium, in the presence of bromide ion the benzyl carbon might be attacked by bromide ion from both the inner and outer sides. Though intermediate A could easily collapse back to (S)-3, the intermediate B must rotate its bond to recyclize to (R)-3. This process would obviously enhance the chance of racemization. (Matrix Presented)
14. Chiral GC was performed with cp-Cyclodex-236 M column; column temperature: 161°C; retention time of (-)-3: 11.82 min; retention time of (+)-3: 12.13 min.
15. (a) Denmark, S. E.; O'Connor, S. E. J. Org. Chem. 1997, 62, 584-594;
16. (b) Denmark, S. E.; O'Connor, S. E. J. Org. Chem. 1997, 62, 3390-3401;
17. (c) Brookhart, M.; Studabaker, W. B. Chem. Rev. 1987, 87, 411-432.
18. 3, c=0.25).
19. R (-)-isomer: 46.36 min (0%); Daicel OB, i-PrOH:hexane, 10:90, 0.8 mL/min.
20. (a) Obika, S.; Nishiyama, T.; Tatematsu, S.; Miyashita, K.; Imanishi, T. Chem. Lett. 1996, 853-854;
21. (b) Obika, S.; Nishiyama, T.; Tatematsu, S.; Miyashita, K.; Imanishi, T. Tetrahedron 1997, 53, 3073-3082.