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手性铵甜菜碱催化α-芳基硝基甲烷与芳香族N-Boc亚胺的高度立体选择性氮杂亨利反应。

Chiral ammonium betaine-catalyzed highly stereoselective aza-henry reaction of α-aryl nitromethanes with aromatic N-Boc imines.

作者信息

Uraguchi Daisuke, Oyaizu Keigo, Noguchi Haruhiro, Ooi Takashi

机构信息

Institute of Transformative Bio-Molecules (WPI-ITbM) and Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Nagoya 464-8603 (Japan).

出版信息

Chem Asian J. 2015 Feb;10(2):334-7. doi: 10.1002/asia.201402943. Epub 2014 Oct 22.

DOI:10.1002/asia.201402943
PMID:25338974
Abstract

A highly stereoselective aza-Henry reaction of α-aryl nitromethanes with aromatic N-Boc imines was established by using C1 -symmetric chiral ammonium betaine as a bifunctional organic base catalyst. Various substituted aryl groups for both imines and nitromethanes were tolerated in the reaction, and a series of precursors for the synthesis of unsymmetrical anti-1,2-diaryl ethylenediamines was provided.

摘要

通过使用C1对称手性铵甜菜碱作为双功能有机碱催化剂,建立了α-芳基硝基甲烷与芳香族N-Boc亚胺的高度立体选择性氮杂-Henry反应。该反应中,亚胺和硝基甲烷的各种取代芳基均能兼容,并提供了一系列用于合成不对称反式-1,2-二芳基乙二胺的前体。

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