Regioselectivity of Michael Additions to 3??(Pyridin??3??yl or Pyrimidin??2??yl) propenoates and Their N??Oxides–Experimental and Theoretical Studies

E Lewandowska, DC Chatfield

文献索引：Lewandowska, Elzbieta; Chatfield, David C. European Journal of Organic Chemistry, 2005 , # 15 p. 3297 - 3303

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被引用次数: 13

摘要

Abstract We demonstrate that nucleophilic addition to α, β-unsaturated carbonyl compounds can be redirected from the usual β-carbon (Michael) to an α-carbon regioselectivity by attaching a π-deficient aromatic substituent to the β-carbon atom. In particular, propanethiol addition to 3-(pyridin-3-yl or pyrimidin-2-yl) propenoate gives a β-carbon adduct, while addition to the corresponding more π-deficient N-oxides gives the α-adduct or a mixture of ...