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Stereoselective Epoxidation of 4-Deoxypentenosides:  A Polarized-π Model

Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907-2084
Org. Lett., 2006, 8 (20), pp 4545–4548
DOI: 10.1021/ol0617401
Publication Date (Web): August 30, 2006
Copyright © 2006 American Chemical Society

Abstract

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The high facioselectivity in the epoxidation of 4-deoxypentenosides (4-DPs) by dimethyldioxirane (DMDO) correlates with a stereoelectronic bias in the 4-DPs' ground-state conformations, as elucidated by polarized-π frontier molecular orbital (PPFMO) analysis.

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Article Views: 561 Times
Received 15 July 2006
Published online 30 August 2006
Published in print 1 September 2006
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