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Highly stereoselective intramolecular Michael addition using alpha-sulfinyl vinyllithium as an unprecedented Michael
N Maezaki1, S Yuyama, H Sawamoto
1Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan.
Organic Letters
|June 30, 2001
Abstract:
[figure: see text] The first example of an asymmetric intramolecular Michael addition reaction using alpha-lithiated vinylic sulfoxide as a Michael donor is reported. Michael addition of the alpha-lithiated vinylic sulfoxide to (Z)-enoates proceeds with high diastereoselectivity to give the adducts having a stereogenic center with (R)-configuration at the beta-position of the ester in the cyclopentene ring formation. The selectivity was reversed in the six-membered ring formation. On the other hand, the corresponding (E)-enoates provided Michael adducts with poor diastereoselectivity.