N-Boc-aminals as easily accessible precursors for less accessible N-Boc-imines: facile synthesis of optically active propargylamine derivatives using Mannich-type reactions

被引：27

作者：

Yurino, Taiga ^{[1
]}

Aota, Yusuke ^{[1
]}

Asakawa, Daisuke ^{[1
]}

Kano, Taichi ^{[1
]}

Maruoka, Keiji ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Kitashirakawa Oiwake Cho, Kyoto 6068224, Japan

来源：

TETRAHEDRON | 2016年 / 72卷 / 26期

基金：

日本学术振兴会;

关键词：

Aminal; Imine; Mannich reaction; Enantioselective catalysis; ZINC/BINOL-CATALYZED ALKYNYLATION; ENANTIOSELECTIVE BRONSTED ACID; TERMINAL ALKYNES; METAL CATALYSIS; DIRECT-ADDITION; ASYMMETRIC-SYNTHESIS; VINYLOGOUS MANNICH; AMINES; ACTIVATION; AMINATION;

D O I：

10.1016/j.tet.2016.03.076

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We developed a facile and practical synthesis of N-Boc-aminals, which can be used as precursors for less accessible N-Boc-imines. Aminals were obtained via simple dehydration condensation reactions of t-butyl carbamate (BocNH(2)) and various aldehydes in acetic anhydride, followed by filtration and washing with hexane. The obtained N-Boc-alkynylaminals could be successfully applied in enantioselective Mannichtype reactions, catalyzed by chiral phosphoric acids, to afford optically active propargylamine derivatives. (C) 2016 Published by Elsevier Ltd.

引用

页码：3687 / 3700

页数：14

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