Efficient synthesis of beta-hydroxy-alpha-amino acid derivatives via direct catalytic asymmetric aldol reaction of alpha-isothiocyanato imide with aldehydes

Chemistry : a European Journal
Xiaohong ChenXiaoming Feng

Abstract

An easily available and efficient chiral N,N'-dioxide-nickel(II) complex catalyst has been developed for the direct catalytic asymmetric aldol reaction of alpha-isothiocyanato imide with aldehydes which produces the products in morderate to high yields (up to 98 %) with excellent diastereo- (up to >99:1 d.r.) and enantioselectivities (up to >99 % ee). A variety of aromatic, heteroaromatic, alpha,beta-unsaturated, and aliphatic aldehydes were found to be suitable substrates in the presence of 2.5 mol % L-proline-derived N,N'-dioxide L5-nickel(II) complex. This process was air-tolerant and easily manipulated with available reagents. Based on experimental investigations, a possible transition state has been proposed to explain the origin of reactivity and asymmetric inductivity.

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Citations

Dec 22, 2016·Journal of the American Chemical Society·Wei DingWen-Jing Xiao
May 31, 2018·Chemical Society Reviews·Yasuhiro YamashitaShū Kobayashi
Sep 8, 2011·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Shigeki Matsunaga, Tatsuhiko Yoshino
Apr 1, 2015·Angewandte Chemie·Karin WeidnerMasakatsu Shibasaki
Jun 12, 2013·Chemistry : a European Journal·Yi-Ming CaoRui Wang
Jun 29, 2018·The Journal of Organic Chemistry·Pauline ChaumontAnne Harrison-Marchand

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