Efficient one-step aldol-type reaction of ketones with acetals and ketals mediated by dibutylboron triflate/diisopropylethyl amine

被引：16

作者：

Li, LS

Das, S

Sinha, SC

机构：

[1] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA

[2] Scripps Res Inst, Dept Mol Biol, La Jolla, CA 92037 USA

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 01期

关键词：

D O I：

10.1021/ol030108u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly efficient one-step Mukaiyama aldol-type reaction has been developed for the synthesis of beta-alkoxy carbonyl compounds starting from ketones and acetals/ketals. The reaction is mediated by a combination of Bu2BOTf and i-Pr2NEt affording the products in high yields. Formation of the two possible diastereoisomers of the beta-alkoxy ketones from the chiral acetals shows that the condensation takes place by an S(N)1 mechanism, involving prior opening of the acetal to an oxonium ion.

引用

页码：127 / 130

页数：4

共 31 条

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