Abstract
(Equation presented) The conjugate addition reaction of a stable, in situ generated silyllithium gives a β-hydroxysilyl ester with high diastereoselectivity. Conversion of the β-hydroxysilyl ester to a β-fluorosilyl ester affords the precursor to the oxasilacyclopentane acetal in high yields under mild conditions. A hydride reduction and subsequent intramolecular silylation lead to the acetal in excellent yields. Finally, highly selective nucleophilic substitution affords oxasilacyclopentanes, which undergo a mild oxidation to afford 1,3-trans diols with high selectivity.
Original language | English (US) |
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Pages (from-to) | 4325-4327 |
Number of pages | 3 |
Journal | Organic Letters |
Volume | 5 |
Issue number | 23 |
DOIs | |
State | Published - Nov 13 2003 |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry