Catalytic asymmetric diazoacetate cyclopropanation of 1-tosyl-3- vinylindoles. A route to conformationally restricted homotryptamines

Organic Letters

Volumn 7, Issue 13, 2005, Pages 2651-2654

  Marcin, Lawrence R ^a   Denhart, Derek J ^a   Mattson, Ronald J ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 (5 CYANO 1H INDOL 3 YL) 1 (N,N DIMETHYLAMINOMETHYL)CYCLOPROPANE; 2-(5-CYANO-1H-INDOL-3-YL)-1-(N,N-DIMETHYLAMINOMETHYL)CYCLOPROPANE; ACETIC ACID DERIVATIVE; AZO COMPOUND; CYCLOPROPANE DERIVATIVE; INDOLE DERIVATIVE; TOLUENESULFONIC ACID DERIVATIVE; TRYPTAMINE DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; SYNTHESIS;

ACETATES; AZO COMPOUNDS; CATALYSIS; CYCLIZATION; CYCLOPROPANES; INDOLES; MOLECULAR STRUCTURE; TOSYL COMPOUNDS; TRYPTAMINES; VINYL COMPOUNDS;

EID: 24944442746     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050790n     Document Type: Article

References (25)

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19. 2), because of its widespread utility and ease of preparation. See ref 7a.
20. 3 protons relative to the same protons of the cis product.
21. Enantiomeric excess of the cis diastereomer was not determined, since an analytical method for its chiral HPLC separation was not developed.
22. In the case of styrene, the use of bulky diazoesters has been documented to improve both the diastereo- and enantioselectivity of the reaction. See ref 7b.
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24. A manuscript detailing a highly optimized synthesis of BMS-505130 on a kilogram scale using the catalytic asymmetric diazoacetate cyclopropanation is currently in preparation.
25. Mattson, R. J.; Denhart, D. J.; Marcin, L. R.; Higgins, M. A.; Ditta, J. L.; Deskus, J. A.; Catt, J. D.; Sloan, C. P.; Beno, B. R.; Gao, Q.; Molski, T. F.; Mattson, G. K.; Taber, M. T.; Lodge, N. J. Manuscript submitted.