Enantioselective Syntheses of (Z)-6′-Boryl-anti-1,2-oxaborinan-3-enes via a Dienylboronate Protoboration and Asymmetric Allylation Reaction Sequence

被引：25

作者：

Chen, Jichao ^{[1
]}

Chen, Ming ^{[1
]}

机构：

[1] Auburn Univ, Dept Chem & Biochem, Auburn, AL 36849 USA

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 18期

关键词：

CHIRAL BRONSTED ACID; HIGHLY STEREOSELECTIVE-SYNTHESIS; CARBON BOND FORMATION; HOMOALLYLIC ALCOHOLS; PHOSPHORIC-ACID; CATALYZED ALLYLBORATION; ALDEHYDE ALLYLBORATION; MECHANISTIC INSIGHTS; REAGENTS; KETONES;

D O I：

10.1021/acs.orglett.0c02657

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantioselective synthesis of 6'-boryl-anti-1,2-oxaborinan-3-enes is reported. A Cu-catalyzed highly stereo-selective 1,4-protoboration of 1,1-bisboryl-1,3-butadiene is developed to generate (E)-alpha,delta-bisboryl-crotylboronate. The chiral phosphoric-acid-catalyzed asymmetric allylboration of aldehydes with the boron reagent produces 6'-boryl-anti-1,2-oxaborinan-3-enes with excellent Z-selectivities and enantioselectivities. The product contains a vinyl and alkyl boronate unit that can directly participate in a variety of subsequent transformations.

引用

页码：7321 / 7326

页数：6

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