Enantioselective Synthesis of 2,2,5-Tri- and 2,2,5,5-Tetrasubstituted Tetrahydrofurans via [4+2] Cycloaddition and Ring-Opening Cross-Metathesis

被引：15

作者：

Benjamin, Noah M. ^{[1
]}

Martin, Stephen F. ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 03期

关键词：

DIELS-ALDER REACTIONS; DESULFONYLATION REACTIONS; DOMINO METATHESIS; OXYALLYL CATIONS; FORMAL SYNTHESIS; DERIVATIVES; 7-OXANORBORNENES; ALLENAMIDES; ALDEHYDES; FURAN;

D O I：

10.1021/ol102798f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A chiral vinyl sulfoxide has been developed that undergoes highly diastereoselective Diels-Alder cycloadditions with various substituted furans in excellent yield. The cycloadducts can be stereoselectively transformed Into 2,2,5-tri- and 2,2,5,5-tetrasubstituted tetrahydrofurans, which are structural subunits of many natural products, via regioselective ring-opening metathesis/cross-metathesis or oxidative cleavage/refunctionalization.

引用

页码：450 / 453

页数：4

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