Tetrahedron

Asymmetric michael additions of ester enolates to enantiomerically pure vinylic sulfoxides: synthesis of 3-substituted glutarate esters in high enantiomeric purity

…, M Weitzberg, TG Hamill, E Asirvatham, H Cun-Heng…

Index: Posner, Gary H.; Weitzberg, Moshe; Hamill, Terence G.; Asirvatham, Edward; Cun-heng, He; Clardy, John Tetrahedron, 1986 ,  vol. 42,  # 11  p. 2919 - 2929

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Citation Number: 77

Abstract

Various ester enolate ions add as Michael donors to enantiomerically pure Michael acceptor cycloalkenone sulfoxides 1a and 1b and unsaturated lactone sulfoxides 3a and 3b. The level of asymmetric induction in some cases is extraordinarily high (95% ee of final 1, 5- dicarbonyl products). Adduct ester lactones 5 and 6 can be converted easily into some synthetically versatile, trifunctional, 3-substituted glutarate esters of high enantiomeric ...