Highly Stereoselective Intramolecular Michael Addition Using α-Sulfinyl Vinyllithium as an Unprecedented Michael Donor
2000-12-05T00:00:00Z (GMT) by
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 (<i>Z</i>)-enoates proceeds with high diastereoselectivity to give the adducts having a stereogenic center with (<i>R</i>)-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 (<i>E</i>)-enoates provided Michael adducts with poor diastereoselectivity.
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