Facile Domino Access to Chiral Mono-, Bi-, and Tricyclic 2,3-Dihydrofurans

被引：85

作者：

Fan, Li-Ping ^{[1
]}

Li, Ping ^{[1
]}

Li, Xin-Sheng ^{[1
]}

Xu, Dong-Cheng ^{[1
]}

Ge, Meng-Meng ^{[1
]}

Zhu, Wei-Dong ^{[1
]}

Xie, Jian-Wu ^{[1
]}

机构：

[1] Zhejiang Normal Univ, Dept Chem & Life Sci, Minist Educ Adv Catalysis Mat, Key Lab, Jinhua 321004, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 24期

基金：

中国国家自然科学基金;

关键词：

ISOXAZOLINE N-OXIDE; ASYMMETRIC-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; 1,3-DICARBONYL COMPOUNDS; CONJUGATE ADDITION; BETA-NITROSTYRENES; CARBONYL-COMPOUNDS; MICHAEL ADDITION; NATURAL-PRODUCTS; THIOUREA;

D O I：

10.1021/jo101935k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric domino Michael-S(N)2 reaction of various 1,3-dicarbonyl compounds to alpha-bromonitroalkenes is described for the first time, employing readily available cinchona-derived bifunctional thioureas as organocatalysts. The novel transformations were highly regio-, chemo-, diastereo-, and enantioselective, which simultaneously gave the chiral tricyclic 2,3-dihydrofurans, bicyclic 2,3-dihydrofurans, and tetrasubstituted 2,3-dihydrofurans with two vicinal chiral carbon centers.

引用

页码：8716 / 8719

页数：4

共 64 条

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Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677

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