%0 Journal Article %A Maezaki, Naoyoshi %A Yuyama, Sachiko %A Sawamoto, Hiroaki %A Suzuki, Tomoko %A Izumi, Mayuko %A Tanaka, Tetsuaki %D 2000 %T Highly Stereoselective Intramolecular Michael Addition Using α-Sulfinyl Vinyllithium as an Unprecedented Michael Donor %U https://acs.figshare.com/articles/journal_contribution/Highly_Stereoselective_Intramolecular_Michael_Addition_Using_-Sulfinyl_Vinyllithium_as_an_Unprecedented_Michael_Donor/3737550 %R 10.1021/ol006697a.s001 %2 https://acs.figshare.com/ndownloader/files/5829318 %K Stereoselective Intramolecular Michael Addition %K Michael adducts %K Michael addition %K intramolecular Michael addition reaction %K cyclopentene ring formation %K Michael donor %K stereogenic center %K Unprecedented Michael Donor %X 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. %I ACS Publications