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

Lawrence R Marcin; Derek J Denhart; Ronald J Mattson

doi:10.1021/ol050790n

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

Org Lett. 2005 Jun 23;7(13):2651-4. doi: 10.1021/ol050790n.

Authors

Lawrence R Marcin¹, Derek J Denhart, Ronald J Mattson

Affiliation

¹ Discovery Chemistry, Bristol-Myers Squibb Pharmaceutical Research Institute, Wallingford, Connecticut 06492, USA. [email protected]

PMID: 15957913
DOI: 10.1021/ol050790n

Abstract

[reaction: see text] Substituted 1-tosyl-3-vinylindoles undergo catalytic asymmetric cyclopropanation with ethyl- and tert-butyldiazoacetate to afford N-protected trans-2-(indol-3-yl)-1-cyclopropanecarboxylic esters in good yield and high enantiomeric excess (81-88% ee). The resulting cycloadducts are demonstrated to be useful intermediates for the synthesis of conformationally restricted, homotryptamine-like analogues such as BMS-505130.

MeSH terms

Acetates / chemistry
Azo Compounds / chemistry*
Catalysis
Cyclization
Cyclopropanes / chemical synthesis*
Indoles / chemical synthesis*
Indoles / chemistry*
Molecular Structure
Tosyl Compounds / chemistry*
Tryptamines / chemical synthesis*
Vinyl Compounds / chemistry*

Substances

2-(5-cyano-1H-indol-3-yl)-1-(N,N-dimethylaminomethyl)cyclopropane
Acetates
Azo Compounds
Cyclopropanes
Indoles
Tosyl Compounds
Tryptamines
Vinyl Compounds