Functionalised bicyclic alcohols by enantioselective α-deprotonation–rearrangement of meso-epoxides†
- 24 August 2001
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 18,p. 2161-2174
- https://doi.org/10.1039/b105369h
Abstract
Enantioselective α-deprotonation–rearrangement of achiral substituted cyclooctene oxides 7, 27 and 28 and N-Boc hexahydroazonine oxide 45 using organolithiums in the presence of (−)-sparteine 3 or (−)-α-isosparteine 4 gives the functionalised bicyclo[3.3.0]octan-2-ols 9, 29, and 32 and indolizinol 47 in 50–72% yields and 83–89% ees.Keywords
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