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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 31, 2001 - Issue 6
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Original Articles

DETERMINANTS OF DIASTEREOSELECTIVITY IN -BENZYLATION REACTIONS OF CARBOXYLIC ESTERS OF BORNANOL DERIVATIVES

Melanie D. Evans Department of Chemistry, Rhodes University, P.O. Box 94, 6140, Grahamstown, Republic of South Africa
&
Perry T. Kaye Department of Chemistry, Rhodes University, P.O. Box 94, 6140, Grahamstown, Republic of South Africa
Pages 805-815 | Received 01 Jun 2000, Published online: 09 Nov 2006
 
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Abstract

The influence of the steric bulk and chelation potential of the “blocking group” on the unexpectedly low diastereoselectivity observed during the α-benzylation of carboxylic ester enolates of 3,3-(2,3-butanedioxy)-2-exo-bornanol is examined.

ACKNOWLEDGMENTS

The authors thank AECI Ltd. and the National Research Foundation (NRF) for a bursar (to M.D.E.), and the NRF and Rhodes University for generous financial support.

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