手性布朗斯特酸催化的对映选择性直接氮杂杂环狄尔斯-阿尔德反应

Enantioselective direct aza hetero-Diels-Alder reaction catalyzed by chiral Brønsted acids.

作者信息

Liu Hua, Cun Lin-Feng, Mi Ai-Qiao, Jiang Yao-Zhong, Gong Liu-Zhu

机构信息

Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, 230026, China.

出版信息

Org Lett. 2006 Dec 21;8(26):6023-6. doi: 10.1021/ol062499t.

DOI:10.1021/ol062499t

PMID:17165920

Abstract

[Structure: see text] The first chiral Brønsted acid-catalyzed asymmetric direct aza hetero-Diels-Alder reaction has been described. The phosphoric acids, prepared from binol and H8-binol derivatives, have shown catalytic ability for the reaction of cyclohexenone with N-PMP-benzaldimine. A chiral phosphoric acid, derived from 3,3-di(4-chloropheneyl)-H8-binol, exhibited superior enantioselectivity, affording fairly good yields and enantioselectivities for the reaction of a range of aromatic aldimines with cyclohexenone.

摘要

[结构：见正文] 首次报道了手性布朗斯特酸催化的不对称直接氮杂杂Diels-Alder反应。由联萘酚和H8-联萘酚衍生物制备的磷酸已显示出对环己烯酮与N-PMP-苯甲醛亚胺反应的催化能力。一种由3,3-二(4-氯苯基)-H8-联萘酚衍生的手性磷酸表现出优异的对映选择性，对于一系列芳香醛亚胺与环己烯酮的反应提供了相当好的产率和对映选择性。