N,N-DIALKYLTHIOAMIDES IN THE MICHAEL ADDITION TO CONJUGATE CARBONYL COMPOUNDS, REGIOSELECTIVITY, STEREOCHEMISTRY AND MECHANISM

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Abstract
The regio- and diastereoselectivity of the addition of N,N-dialkylphenylthioacetamide enolates to some conjugate carbonyl compounds are studied. The results are compared with oxoanalogs and the differences are rationalized in terms of specific behaviour of sulfur. General trend to 1,4-addition is demonstrated. The stereochemistry is correlated with the cyclic transition state taking into account the ground state conformation preferred by the acceptor.