铱催化的N-叔丁氧羰基氮杂苯并降冰片二烯与仲胺亲核试剂的不对称开环反应。

Iridium-catalyzed asymmetric ring-opening reactions of N-Boc-azabenzonorbornadiene with secondary amine nucleophiles.

作者信息

Yang Dingqiao, Long Yuhua, Wang Huan, Zhang Zhenming

机构信息

School of Chemistry and Environment, South China Normal University, Guangzhou 510006, China.

出版信息

Org Lett. 2008 Nov 6;10(21):4723-6. doi: 10.1021/ol801768e. Epub 2008 Oct 4.

DOI:10.1021/ol801768e

PMID:18834138

Abstract

Iridium-catalyzed asymmetric ring-opening reactions of N-Boc-azabenzonorbornadiene with a number of secondary amines has been developed for the first time. The reaction gave 1,2-trans-diamine derivatives in moderate to good yields with high enantioselectivity in the presence of 2.5 mol % of [Ir(COD)Cl]2 and 5 mol % of (S)-BINAP. The trans-configuration of the 1,2-diamino products was confirmed by X-ray crystallography.

摘要

首次开发了铱催化的N - Boc - 氮杂苯并降冰片二烯与多种仲胺的不对称开环反应。在2.5 mol%的[Ir(COD)Cl]₂和5 mol%的(S)-BINAP存在下，该反应以中等至良好的产率和高对映选择性得到1,2 - 反式二胺衍生物。通过X射线晶体学确定了1,2 - 二氨基产物的反式构型。