Stereocontrolled Synthesis of 1,2-and 1,3-Diamine Building Blocks from Aziridine Aldehyde Dimers

被引：38
|
作者：
Liew, Sean K. [1 ]
He, Zhi [1 ]
Denis, Jeffrey D. St. [1 ]
Yudin, Andrei K. [1 ]
机构：
[1] Univ Toronto, Dept Chem, Davenport Res Labs, Toronto, ON M5S 3H6, Canada
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 23期
基金：
加拿大自然科学与工程研究理事会;
关键词：
ORGANOBORONIC ACIDS; MANNICH REACTION; AMINES; REACTIVITY; EFFICIENT; REAGENTS; DIAMINES; ALCOHOLS; ESTERS;
D O I：
10.1021/jo401489q
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Vicinal aziridine-containing diamines have been obtained with high syn-stereoselectivity from readily available aziridine aldehyde dimers in the Petasis borono-Mannich reaction. Subsequent solvent- and/or nucleophile-dependent ring-opening of the aziridine ring yields functionalized 1,2- and 1,3-diamines with high regioselectivity. The ring opening is also influenced by the substitution at the C3 position of the aziridine. A mechanistic rationale for the highly syn-selective three-component reaction is proposed.
引用
收藏
页码：11637 / 11645
页数：9
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