Isothiourea-catalyzed formal enantioselective conjugate addition of benzophenone imines to β-fluorinated α,β-unsaturated esters†,10.1039/D2CC01936A

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Lactoyl-CoA 全氟丁基戊烷白叶藤碱全氟己基辛烷新白叶藤碱壳寡糖特色专题-生物多肽

Isothiourea-catalyzed formal enantioselective conjugate addition of benzophenone imines to β-fluorinated α,β-unsaturated esters†

Jerson E. Lapetaje,Claire M. Young,Chang Shu,Andrew D. Smith

Chemical Communications Pub Date : 05/20/2022 00:00:00 , DOI:10.1039/D2CC01936A

Abstract

The isothiourea-catalyzed formal enantioselective conjugate addition of 2-hydroxybenzophenone imine derivatives to α,β-unsaturated para-nitrophenyl esters has been developed. Investigations of the scope and limitations of this procedure showed that β-electron withdrawing substituents within the α,β-unsaturated ester component are required for good product yield, giving rise to a range of β-imino ester and amide derivatives in moderate to good isolated yields with excellent enantioselectivity (20 examples, up to 81% yield and 97 : 3 er).