4.8 Article

Stereoselective epoxidation of 4-deoxypentenosides:: A polarized-π model

Journal

ORGANIC LETTERS
Volume 8, Issue 20, Pages 4545-4548

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol0617401

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Funding

  1. NIGMS NIH HHS [GM-06982-01, R01 GM069862, R01 GM069862-04] Funding Source: Medline

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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-pi frontier molecular orbital (PPFMO) analysis.

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