Investigation of the diastereoselective cyclization of bis-sulfonyl esters.
[reaction: see text] The diastereoselective cyclization of bissulfonyl esters was investigated by varying both the size and the placement of the substituent on the tether adjoining the reacting centers. Substitution at either the alpha or beta position relative to the ester moiety gave diastereomeric ratios of (1-3):1, while gamma substitution dramatically increased the diastereomeric ratios to (6-20):1.
Colucci
John
J
Department of Medicinal Chemistry, Merck Frosst Centre for Therapeutic Research, Merck Frosst Canada & Co., P.O. Box 1005, 16711 Trans Canada Highway, Kirkland, Quebec, Canada H9H 3L1. john_colucci@merck.com
Lee
David
D
Wilson
Marie-Claire
MC
Chau
Ann
A