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
收藏
页码：2546 / 2549
页数：4
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