Functionalized bicyclo[3.3.0]octanes by enantioselective transannular desymmetrization.
[figure: see text] Enantioselective alpha-deprotonation-rearrangement of achiral substituted cyclooctene oxides 7, 17, and 18 using organolithiums in the presence of (-)-sparteine (3) or (-)-alpha-isosparteine (4) gives the functionalized bicyclo[3.3.0]octan-2-ols 8, 19, and 20 in 56-72% yields and 83-89% ee's.
Hodgson
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Dyson Perrins Laboratory, Department of Chemistry, University of Oxford, South Parks Road, Oxford, U.K. OX1 3QY. david.hodgson@chem.ox.ac.uk
Cameron
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