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Highly Stereoselective Intramolecular Michael Addition Using α-Sulfinyl Vinyllithium as an Unprecedented Michael Donor

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journal contribution
posted on 05.12.2000 by Naoyoshi Maezaki, Sachiko Yuyama, Hiroaki Sawamoto, Tomoko Suzuki, Mayuko Izumi, Tetsuaki Tanaka
The first example of an asymmetric intramolecular Michael addition reaction using α-lithiated vinylic sulfoxide as a Michael donor is reported. Michael addition of the α-lithiated vinylic sulfoxide to (Z)-enoates proceeds with high diastereoselectivity to give the adducts having a stereogenic center with (R)-configuration at the β-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.