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

页码：11637 / 11645

页数：9

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