Highly Chemo-, Enantio-, and Regioselective Synthesis of α,α-Disubstituted Furanones by Cu-Catalyzed Conjugate Addition

被引：17

作者：

Endo, Kohei ^{[1
,2
]}

Yakeishi, Sayuri ^{[3
]}

Takayama, Ryotaro ^{[3
]}

Shibata, Takanori ^{[3
]}

机构：

[1] Kanazawa Univ, Grad Sch Nat Sci & Technol, Dept Chem, Kanazawa, Ishikawa 9201192, Japan

[2] PRESTO Japan Sci & Technol Agcy JST, Kawaguchi, Saitama 3320012, Japan

[3] Waseda Univ, Grad Sch Sci & Technol, Dept Chem & Biochem, Shinjuku Ku, Tokyo 1698555, Japan

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2014年 / 20卷 / 29期

关键词：

addition reactions; aluminum; asymmetric synthesis; copper; heterocyclic compounds; QUATERNARY STEREOGENIC CENTERS; SUBSTITUTED CYCLIC ENONES; ENANTIOSELECTIVE ALPHA-ARYLATION; ASYMMETRIC ALLYLIC ALKYLATION; ARYL ALUMINUM REAGENTS; TRISUBSTITUTED ENONES; ORGANOZINC REAGENTS; GRIGNARD-REAGENTS; CHIRAL CENTERS; MONO-PHOS;

D O I：

10.1002/chem.201403446

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly chemo-, enantio-, and regioselective synthesis of furanones bearing an alpha,alpha- disubstituted quaternary stereogenic center is reported. The Cu-catalyzed enantioselective conjugate addition of organoaluminum reagents to unsaturated ketoesters at room temperature and subsequent lactonization took place. Synthetic transformations of furanones represent facile approaches to various cyclic or acyclic compounds bearing a quaternary stereogenic center.

引用

页码：8893 / 8897

页数：5

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