Chemo- and Stereoselective Crotylation of Aldehydes and Cyclic Aldimines with Allylic gem-Diboronate Ester

被引：64

作者：

Park, Jinyoung ^{[1
]}

Choi, Seoyoung ^{[1
]}

Lee, Yeosan ^{[1
]}

Cho, Seung Hwan ^{[1
]}

机构：

[1] Pohang Univ Sci & Technol POSTECH, Dept Chem, Pohang 37673, South Korea

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 15期

基金：

新加坡国家研究基金会;

关键词：

CATALYTIC ENANTIOSELECTIVE ALLYLATION; ANTI-HOMOALLYLIC ALCOHOLS; CHIRAL PHOSPHORIC-ACID; ASYMMETRIC ALLYLBORATION; ORGANIC-SYNTHESIS; BORONIC ESTERS; DIASTEREOSELECTIVE SYNTHESIS; ALPHA-KETOESTERS; ROOM-TEMPERATURE; TERMINAL ALKYNES;

D O I：

10.1021/acs.orglett.7b01821

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report a highly chemo- and stereoselective crotylation of aldehydes and cyclic aldimines with allylic-gem-diboronate ester as a new type of organoboron reagent. The allylic-gem-diboronate ester undergoes the crotylation with aldehydes and cyclic aldimines in excellent stereoselectivity, forming anti-5,6-disubstituted oxaborinin-2-ols or (E)-delta-boryl-anti-homoallylic amines in high efficiency. The reaction shows a wide range of substrate scope and excellent functional group tolerance. The synthetic applications of the obtained products, including stereospecific C-C, C-O, and C-Cl bond formation, are also demonstrated.

引用

页码：4054 / 4057

页数：4

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