Asymmetric Aldol Reaction of Allenoates: Regulation for the Selective Formation of Isomeric Allenyl or Alkynyl Aldol Adduct

被引：15

作者：

Bang, Jiyun ^{[1
]}

Kim, Hyuna ^{[1
]}

Kim, Jihyun ^{[1
]}

Yu, Chan-Mo ^{[1
]}

机构：

[1] Sungkyunkwan Univ, Dept Chem, Suwon 440746, South Korea

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 06期

基金：

新加坡国家研究基金会;

关键词：

DELTA-LACTONES; MESO-EPOXIDES; IMINES; CATALYSIS; ESTERS; AUXILIARIES; CYCLIZATION; PROPARGYL; CARBINOLS; ALDEHYDES;

D O I：

10.1021/acs.orglett.5b00454

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly stereoselective synthesis of 3-butynyl-threo-aldol adducts is achieved from the reaction of allyl allenoate with a chiral bromoborane in the presence of iPr(2)NEt, followed by addition of BF3OEt2 as an additive to scavenge excess base and then aldehydes, whereas isomeric allenyl aldol adducts are formed in the absence of a Lewis acid additive from methyl allenoate.

引用

页码：1573 / 1576

页数：4

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