Mechanism and applications of lithium amide-induced asymmetric rearrangements of 4-substituted and 4,4-disubstituted cyclopentene oxides to cyclopentenols
- 1 January 1999
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 24,p. 3579-3590
- https://doi.org/10.1039/a907522d
Abstract
The preparation and lithium amide-induced rearrangements of 1,2-dideuterated 4-substituted cyclopentene oxides 11 and 19 are described, providing insight into the deprotonation mechanisms operating in such systems. Highly enantioselective syntheses of 4-substituted cis-4-hydroxymethylcyclopent-2-en-1-ols 32a–c are described. Also described are asymmetric syntheses of prostaglandin precursor 40 and (+)-iridomyrmecin (48) via highly enantioselective rearrangement of the epoxide 3 and subsequent Ireland–Claisen rearrangement.Keywords
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