Gold-catalyzed hydrofunctionalization of allenes with nitrogen and oxygen nucleophiles and its mechanistic insight

被引：93

作者：

Nishina, Naoko ^{[1
]}

Yamamoto, Yoshinori ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan

来源：

TETRAHEDRON | 2009年 / 65卷 / 09期

关键词：

Gold-catalysis; Hydrofunctionalization; Hydroamination; Hydroalkoxylation; Chirality transfer; Allene; Allylic amine; Allylic ether; GOLD(I)-CATALYZED INTRAMOLECULAR HYDROAMINATION; ANTI-MARKOVNIKOV HYDROAMINATION; IV METAL-COMPLEXES; INTERMOLECULAR HYDROAMINATION; TRANSITION-METAL; 2-PROPYNYL-1,3-DICARBONYL COMPOUNDS; AMINATION/ANNULATION REACTIONS; HYDROARYLATION REACTIONS; UNACTIVATED ALKENES; ALPHA-AMINOALLENES;

D O I：

10.1016/j.tet.2008.11.106

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A wide range of nucleophiles, such as amines and alcohols, reacted intermolecularly with various allenes in the presence of gold catalysts to give the corresponding hydrofunctionalization products in high yields. The intermolecular hydroamination of chiral allenes with aromatic and aliphatic amines proceeded with high to good enantioface selectivities to afford the corresponding chiral allylic amines. On the other hand, in the case of the intermolecular hydroalkoxylation of chiral allenes, no chirality transfer was observed. This marked contrast on the chirality transfer indicates that the mechanisms of gold-catalysis between hydroamination and hydroalkoxylation are different. (C) 2008 Published by Elsevier Ltd.

引用

页码：1799 / 1808

页数：10

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