An asymmetric ammonia synthon for Michael additions

JM Hawkins, TA Lewis

Index: Hawkins, Joel M.; Lewis, Timothy A. Journal of Organic Chemistry, 1992 , vol. 57, # 7 p. 2114 - 2121

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Citation Number: 55

Abstract

The highly diastereoselective 1, 4-addition of lithiated chiral amine 1 to a,@-unsaturated esters, followed by hydrogenolysis of the benzylic-type CN bonds of the 1, 4-adducts, provides an asymmetric ammonia synthon for Michael additions. Under optimized conditions, lithiated 1 adds to a,@-unsaturated tert-butyl esters in dimethoxyethane at-63" C in high yield with very high diastereoselectivity. Small, large, functionalized, and chiral@- ...