Homoallylboration of Aldehydes: Stereoselective Synthesis of Allylic-Substituted Alkenes and E-Alkenes

被引：0

作者：

Polyak, Daniel ^{[1
]}

Xu, Bokai ^{[1
]}

Krauss, Isaac J. ^{[1
]}

机构：

[1] Brandeis Univ, Dept Chem, Waltham, MA 02454 USA

来源：

ORGANIC LETTERS | 2022年 / 24卷 / 25期

基金：

美国国家科学基金会;

关键词：

NICKEL-CATALYZED HOMOALLYLATION; BORONIC ESTERS; HOMOLOGATION; CYCLIZATION; HOMOCROTYLBORATION; B(C6F5)(3); 1,3-DIENES; REAGENTS; BORANES;

D O I：

10.1021/acs.orglett.2c01789

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclopropanated allylboration reagents participate in the homoallylation of aliphatic and aromatic aldehydes, generating substituted alkenes that are difficult to produce via other methods. In this study, we explored the scope and reactivity of homoallylation with cyclopropylcarbinylboronates bearing various aliphatic and aromatic alpha- and gamma-substituents. alpha-Alkyl substituted boronates afforded E-disubstituted alkenyl secondary alcohols in high enantiomeric ratios, while aryl substituents promoted rearrangement. gamma-Alkyl substituents all resulted in diastereoselective homoallylation, while aryl substitution changed the outcome to cyclopropylcarbinylation.

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页码：4656 / 4659

页数：4

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