Enantioselective C-H Crotylation of Primary Alcohols via Hydrohydroxyalkylation of Butadiene

被引：295

作者：

Zbieg, Jason R. ^{[1
]}

Yamaguchi, Eiji ^{[1
]}

McInturff, Emma L. ^{[1
]}

Krische, Michael J. ^{[1
]}

机构：

[1] Univ Texas Austin, Dept Chem & Biochem, Austin, TX 78712 USA

来源：

SCIENCE | 2012年 / 336卷 / 6079期

关键词：

TRANSITION-METAL CATALYSIS; OXIDATION LEVEL; TRANSFER HYDROGENATION; CARBONYL CROTYLATION; BRONSTED ACID; ALDEHYDES; ALLYLATION; REAGENTS; KETONES; COMPLEXES;

D O I：

10.1126/science.1219274

中图分类号：

O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];

学科分类号：

07 ; 0710 ; 09 ;

摘要：

The direct, by-product-free conversion of basic feedstocks to products of medicinal and agricultural relevance is a broad goal of chemical research. Butadiene is a product of petroleum cracking and is produced on an enormous scale (about 12 x 10(6) metric tons annually). Here, with the use of a ruthenium catalyst modified by a chiral phosphate counterion, we report the direct redox-triggered carbon-carbon coupling of alcohols and butadiene to form products of carbonyl crotylation with high levels of anti-diastereoselectivity and enantioselectivity in the absence of stoichiometric by-products.

引用

页码：324 / 327

页数：4

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