通过手性 N-氨基环氨基甲酸酯腙实现手性酮的不对称反羟醛加成反应。

Asymmetric anti-aldol addition of achiral ketones via chiral N-amino cyclic carbamate hydrazones.

机构信息

Department of Chemistry, University of Houston, Houston, Texas 77204-5003, USA.

出版信息

Chem Commun (Camb). 2013 Sep 4;49(68):7495-7. doi: 10.1039/c3cc44716b.

Abstract

The asymmetric anti-aldol addition of ketone-derived donors and aldehyde acceptors is described. Asymmetric induction is achieved through the use of chiral N-amino cyclic carbamate (ACC) auxiliaries. The transformation exhibits essentially perfect anti-diastereoselectivity and enantioselectivity, and has the unusual feature of proceeding via thermodynamic, rather than kinetic control.

摘要

酮衍生供体和醛受体的不对称反羟醛加成反应被描述。通过使用手性 N-氨基环碳酸酯 (ACC) 助剂实现了不对称诱导。该转化表现出几乎完美的反非对映选择性和对映选择性，并且具有通过热力学而不是动力学控制进行的不寻常特征。