Diastereocontrol in Asymmetric Allyl-Allyl Cross-Coupling: Stereocontrolled Reaction of Prochiral Allylboronates with Prochiral Allyl Chlorides

被引：96

作者：

Brozek, Laura A. ^{[1
]}

Ardolino, Michael J. ^{[1
]}

Morken, James P. ^{[1
]}

机构：

[1] Boston Coll, Dept Chem, Merkert Chem Ctr, Chestnut Hill, MA 02467 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 42期

基金：

美国国家科学基金会;

关键词：

CATALYZED SIGMATROPIC REARRANGEMENTS; COPE REARRANGEMENT; REDUCTIVE ELIMINATION; BOND FORMATION; ALKYLATION; COMPLEXES; ALLYLSILANES; ALDEHYDES; ALCOHOLS; LIGANDS;

D O I：

10.1021/ja2075967

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Palladium-catalyzed allyl-ally cross-coupling was investigated with substituted prochiral allylic boronates. These reactions deliver products bearing adjacent stereocenters, and the issue of diastereocontrol is therefore paramount. Under appropriately modified conditions, this allyl allyl coupling strategy was found to apply to a range of substrates, generally occurring with high enantioselectivity (92:8 to >99:1 er) and good diastereoselection (4:1 to 14:1 dr).

引用

页码：16778 / 16781

页数：4

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