Gold-catalyzed intermolecular hydroalkoxylation of allenes; difference in mechanism between hydroalkoxylation and hydroamination

被引：61

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 LETTERS | 2008年 / 49卷 / 33期

关键词：

alcohol; allene; chirality transfer; gold catalysis; hydroalkoxylation; allylic ether; silver triflate; gold chloride;

D O I：

10.1016/j.tetlet.2008.05.152

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A wide range of alcohols 2 react with various allenes 1 in the presence of ClAuPPh3/AgOTf catalyst at ambient temperature without solvent to produce allylic ethers 3. Contrary to the hydroamination, which proceeds through high chiral-face selectivity for chiral allenes to give the corresponding chiral allylic amines, transfer of chirality is not observed in the hydroalkoxylation, suggesting that the mechanism of the gold-catalyzed hydroalkoxylation is different from that of hydroamination. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：4908 / 4911

页数：4

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