Stereocontrolled synthesis of trisubstituted cyclopropanes: Expedient, atom-economical, asymmetric syntheses of (+)-bicifadine and DOV21947

Organic Letters

Volumn 8, Issue 17, 2006, Pages 3885-3888

  Xu, Feng ^a   Murry, Jerry A ^a   Simmons, Bryon ^a   Corley, Edward ^a   Fitch, Kenneth ^a   Karady, Sandor ^a   Tschaen, David ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 (3,4 DICHLOROPHENYL) 3 AZABICYCLO (3.1.0)HEXANE HYDROCHLORIDE; 1-(3,4-DICHLOROPHENYL)-3-AZABICYCLO-(3.1.0)HEXANE HYDROCHLORIDE; BICIFADINE; CYCLOPROPANE DERIVATIVE; FUSED HETEROCYCLIC RINGS; HETEROCYCLIC COMPOUND; NITRILE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

AZA COMPOUNDS; BICYCLO COMPOUNDS, HETEROCYCLIC; CYCLOPROPANES; MOLECULAR STRUCTURE; NITRILES; STEREOISOMERISM;

EID: 33748631579     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061650w     Document Type: Article

References (19)

1. (a) Sorbera, L. A.; Castaner, J.; Leeson, P. A. Drugs Future 2005, 30, 1.
2. (b) Epstein, J. W.; Brabander, H. J.; Fanshawe, W. J.; Hofmann, C. M.; McKenzie, T. C.; Safir, S. R.; Osterberg, A. C.; Cosulich, D. B.; Lovell, F. M. J. Med. Chem. 1981, 24, 481.
3. Skolnick, P.; Popik, P.; Janowsk, A.; Beer, B.; Lippa, A. Eur. J. Pharmacol. 2003, 461, 99;
4. Life Sci. 2003, 73, 3175.
5. For a superb review, see: Lebel, H.; Marcoux, J. F.; Molinaro, C.; Charette, A. B. Chem. Rev. 2003, 103, 977.
6. For recent examples, see: (a) Kunz, R. K.; MacMillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 3240.
7. (b) Zheng, J.; Liao, W.; Tang, Y.; Sun, X.; Dai, L. J. Am. Chem. Soc. 2005, 127, 12222.
8. (c) Kim, H. Y.; Lurain, A. E.; Garcia-Garcla, P.; Carroll, P. J.; Walsh, P. J. J. Am. Chem. Soc. 2005, 127, 13138.
9. (a) Shuto, S.; Ono, S.; Hase, Y.; Kamiyama, N.; Takada, H.; Yamsihita, K.; Matsuda, A. J. Org. Chem. 1996, 61, 915.
10. (b) For a leading reference of racemic synthesis, see: Langer, P.; Freifeld, I. Org. Lett. 2001, 3, 3903 and references therein.
11. For an example of magnesium halides as Lewis acids to open epoxide, see: Corbel, B.; Durst, T. J. Org. Chem. 1976, 41, 3648.
12. For other examples of using lithium bases, also see: (a) Jeffery, J. E.; Kerrigan, F.; Miller, T. K.; Smith, G. J.; Tometzki, G. B. J. Chem. Soc., Perkin Trans. 1 1996, 2583.
13. (b) Kusumoto, T.; Nakayama, A.; Sato, K.; Hiyama, T.; Takehara, S.; Osawa, M.; Nakamura, K. Chem. Lett. 1992, 2047.
14. (a) (+)-Epichlorohydrin was 98% ee.
15. (b) See Supporting Information.
16. For a recent review, see: Fleming, F. F.; Shook, B. C. Tetrahedron 2002, 58, 1.
17. For leading references, see: (a) Reich, H. J.; Biddle, M. M.; Edmonston, R. J. J. Org. Chem. 2005, 70, 3375.
18. (b) Carlier, P. R.; Lo, C. W. J. Am. Chem. Soc. 2000, 122, 12819 and references therein.
19. - generated from water quenching.