Enantioselective Lewis acid catalyzed Michael reactions of alkylidene malonates.: Catalysis by C2-symmetric bis(oxazoline) copper(II) complexes in the synthesis of chiral, differentiated glutarate esters

被引：168

作者：

Evans, DA ^{[1
]}

Rovis, T ^{[1
]}

Kozlowski, MC ^{[1
]}

Downey, CW ^{[1
]}

Tedrow, JS ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2000年 / 122卷 / 38期

关键词：

D O I：

10.1021/ja002246+

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Ct-symmetric bis(oxazorine)-Cu(TT) complexes 1 catalyze the Mukaiyama Michael reaction of alkylidene malonates and enolsilanes The use of hexafluoro-2-propanol is essential to induce catalyst turnover. High enantioselectivities are exhibited by bulky alkylidene malonate beta-substituents using catalyst la. The glutarate ester products are readily decarboxylated to provide chiral 1,5-dicarbonyl synthons. Crystallographic characterization of substrate-catalyst complexes provides insight into the binding event with these catalysts and affords a rationale for the observed facial selectivities.

引用

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页码：9134 / 9142

页数：9

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