ChemInform Abstract: Highly Stereoselective Intramolecular Michael Addition Using α-Sulfinyl Vinyllithium as an Unprecedented Michael Donor.
Abstract
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ChemInform Abstract
From the examination of the four geometric isomers (Ia) and (IV)-(VI) in the title reaction it is found, that (Z)-enoates (I) and (VI) give cyclopentene sulfoxides (II) with excellent diastereoselectivity and (R)-configuration of the newly formed stereogenic center. (Z)-Enoate (X) affords cyclohexene (IX) also with excellent diastereoselectivity, but with (S)-configuration of the newly formed stereogenic center. (E)-Enoates provide the cycloadducts only with poor diastereoselectivity.
