Enhanced Rate and Selectivity by Carboxylate Salt as a Basic Cocatalyst in Chiral N-Heterocyclic Carbene-Catalyzed Asymmetric Acylation of Secondary Alcohols

S Kuwano, S Harada, B Kang, R Oriez…

Index: Kuwano, Satoru; Harada, Shingo; Oriez, Raphael; Yamada, Ken-Ichi Chemical Communications, 2012 , vol. 48, # 1 p. 145 - 147

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Citation Number: 26

Abstract

The rate and enantioselectivity of chiral NHC-catalyzed asymmetric acylation of alcohols with an adjacent H-bond donor functionality are remarkably enhanced in the presence of a carboxylate cocatalyst. The degree of the enhancement is correlated with the basicity of the carboxylate. With a cocatalyst and a newly developed electron-deficient chiral NHC, kinetic resolution and desymmetrization of cyclic diols and amino alcohols were achieved with ...

~80%

~90%

~34%

~93%

~89%

~72%

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