Asymmetric 1,4-Dihydroxylation of 1,3-Dienes by Catalytic Enantioselective Diboration

被引：140

作者：

Burks, Heather E. ^{[1
]}

Kliman, Laura T. ^{[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 | 2009年 / 131卷 / 26期

关键词：

PLATINUM(0)-CATALYZED DIBORATION; BORON ADDITION; LIGANDS; KETONES; TADDOL; ALLYLBORATION; COMPLEXES; EFFICIENT;

D O I：

10.1021/ja809610h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Asymmetric 1,4-dihydroxytations of 1,3-dienes, and other transformations, are initiated by the Pt-catalyzed enantioselective addition of bis(pinacolato)diboron (B-2(pin)(2)) to conjugated dienes. The studies reported in this communication suggest that both cyclic and acyctic substrates will participate in this reaction; however, dienes which are unable to adopt the S-cis conformation are unreactive. For most substrates, 1,4-addition is the predominant pathway. In addition to oxidation to the derived 2-buten-1,4-diol, stereosetective carbonyl allylation with the intermediate bis(boronate) ester is also described.

引用

页码：9134 / +

页数：3

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