Selective Formation of Adjacent Stereocenters by Allylboration of Ketones under Mild Neutral Conditions

被引：26

作者：

Alam, Rauful ^{[1
]}

Mihai, Raducan ^{[1
]}

Eriksson, Lars ^{[2
]}

Szabo, Kalman J. ^{[1
]}

机构：

[1] Stockholm Univ, Dept Organ Chem, SE-10691 Stockholm, Sweden

[2] Stockholm Univ, Dept Inorgan & Struct Chem, SE-10691 Stockholm, Sweden

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 10期

基金：

瑞典研究理事会;

关键词：

HIGHLY STEREOSELECTIVE-SYNTHESIS; HOMOALLYLIC ALCOHOLS; DIASTEREOSELECTIVE SYNTHESIS; QUATERNARY CENTERS; ASYMMETRIC ALLYLBORATION; ORGANOMETALLIC REAGENTS; CATALYZED SYNTHESIS; ALLYLBORONIC ACIDS; ACYCLIC SYSTEMS; LEWIS-ACID;

D O I：

10.1021/ol401055m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Allylboronic acids readily react with a broad variety of ketones, affording homoallylic alcohols with adjacent quaternary and tertiary stereocenters. The reaction proceeds with very high anti stereoselectivity even if the substituents of the keto group have a similar size. a-Keto acids react with syn stereoselectivity probably due to the formation of acyl boronate intermediates. The allylation reactions proceed without added acids/bases under mild conditions. Because of this, many functionalities are tolerated even with in situ generated allylboronic acids.

引用

页码：2546 / 2549

页数：4

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