Asymmetric synthesis of C-aliphatic homoallylic amines and biologically important cyclohexenylamine analogues

Chi-Lik Ken Lee; Hui Yvonne Ling; Teck-Peng Loh

doi:10.1021/jo048903o

Asymmetric synthesis of C-aliphatic homoallylic amines and biologically important cyclohexenylamine analogues

J Org Chem. 2004 Oct 29;69(22):7787-9. doi: 10.1021/jo048903o.

Authors

Chi-Lik Ken Lee¹, Hui Yvonne Ling, Teck-Peng Loh

Affiliation

¹ Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543.

PMID: 15498019
DOI: 10.1021/jo048903o

Abstract

An efficient method for the asymmetric synthesis of C-aliphatic homoallylic amines with up to 94% yield and 80% de is reported. Ring-closing metathesis of several chiral homoallylic amines using the second-generation Grubbs catalyst provided easy access to a wide variety of cyclohexenylamines.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amines / chemical synthesis*
Catalysis
Crystallography, X-Ray
Cyclization
Cyclohexanes / chemical synthesis*
Cyclohexenes
Imines / chemical synthesis*
Molecular Structure
Stereoisomerism

Substances

Amines
Cyclohexanes
Cyclohexenes
Imines
cyclohexene