Catalytic Enantioselective Synthesis of Tetrahydrofurans: A Dynamic Kinetic Asymmetric [3+2] Cycloaddition of Racemic Cyclopropanes and Aldehydes

被引：286

作者：

Parsons, Andrew T. ^{[1
]}

Johnson, Jeffrey S. ^{[1
]}

机构：

[1] Univ N Carolina, Dept Chem, Chapel Hill, NC 27599 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 09期

基金：

美国国家科学基金会;

关键词：

DONOR-ACCEPTOR CYCLOPROPANES; RING-EXPANSION REACTION; DIASTEREOSELECTIVE SYNTHESIS; ORGANIC-SYNTHESIS; LEWIS-ACID; NITRONES; DERIVATIVES; METHANOCHROMANONE; PYRROLIDINES; INSERTION;

D O I：

10.1021/ja809873u

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly diastereoselective dynamic kinetic asymmetric transformation of racemic 1,1-cyclopropane diesters to prepare enantioenriched tetrahydrofuran (THF) derivatives has been developed. Asymmetric [3 + 2] cycloaddition of activated donor-acceptor (D-A) cyclopropanes and aldehydes catalyzed by ('Bu-pybox)Mgl(2) gives THF products in good to excellent yields (48-92%) as single diastereomers with er's up to 97:3. Aryl, cinnamyl, and aliphatic alclehydes are competent dipolarophiles for this transformation.

引用

页码：3122 / +

页数：3

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