Oxazaborolidinium Ion-Catalyzed Cyclopropanation of α-Substituted Acroleins: Enantioselective Synthesis of Cyclopropanes Bearing Two Chiral Quaternary Centers

被引：97

作者：

Gao, Lizhu ^{[3
]}

Hwang, Geum-Sook ^{[1
,2
]}

Ryu, Do Hyun ^{[3
]}

机构：

[1] Chungnam Natl Univ, Korea Basic Sci Inst, Seoul 136713, South Korea

[2] Chungnam Natl Univ, Grad Sch Analyt Sci & Technol, Seoul 136713, South Korea

[3] Sungkyunkwan Univ, Dept Chem, Suwon 440746, South Korea

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 51期

关键词：

ASYMMETRIC CYCLOPROPANATION; STEREOSELECTIVE CYCLOPROPANATION; DIAZO REAGENTS; CONSTRUCTION; ALKENES; DERIVATIVES; CARBON; ACID; ALKYLATION;

D O I：

10.1021/ja209270e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A catalytic synthetic route to highly functionalized chiral cyclopropane derivatives was developed by Michael-initiated cyclopropanation of alpha-substituted acroleins with aryl- and alkyl diazoacetates. In the presence of chiral (S)-oxazaborolidinium cation 1b as a catalyst, the reaction proceeded in high yield (up to 93%) with high to excellent diastereoselectivity (up to 98% de) and enantio-selectivity (up to 95% ee).

引用

页码：20708 / 20711

页数：4

共 61 条

[51] Ylide-initiated Michael addition-cyclization reactions beyond cyclopropanes [J].

Sun, Xu-Li ;

Tang, Yong .

ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (08) :937-948

[52] Intramolecular [1+4+1] Cycloaddition: Establishment of the Method [J].

Taber, Douglass F. ;

Guo, Pengfei ;

Guo, Na .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (32) :11179-11182

[53] Catalytic enantioselective construction of all-carbon quaternary stereocenters [J].

Trost, BM ;

Jiang, CH .

SYNTHESIS-STUTTGART, 2006, (03) :369-396

[54] Biosynthesis and metabolism of cyclopropane rings in natural compounds [J].

Wessjohann, LA ;

Brandt, W ;

Thiemann, T .

CHEMICAL REVIEWS, 2003, 103 (04) :1625-1647

[55]

Wichmann J, 1999, EUR J ORG CHEM, V1999, P3131

[56] USE OF CYCLOPROPANES AND THEIR DERIVATIVES IN ORGANIC-SYNTHESIS [J].

WONG, HNC ;

HON, MY ;

TSE, CW ;

YIP, YC ;

TANKO, J ;

HUDLICKY, T .

CHEMICAL REVIEWS, 1989, 89 (01) :165-198

[57]

Wu Y., 1996, SYNLETT, P911

[58] Highly Stereoselective C-Silylation and Alkylation of 1-Chlorocyclopropanecarboxylic Ester Using SmI2 [J].

Yoshida, Eri ;

Nagano, Takao ;

Motoyoshiya, Jiro ;

Nishii, Yoshinori .

CHEMISTRY LETTERS, 2009, 38 (11) :1078-1079

[59] Highly Selective Ylide-Initiated Michael Addition/Cyclization Reaction for Synthesis of Cyclohexadiene Epoxide and Vinylcyclopropane Derivatives [J].

Zhu, Ben-Hu ;

Zhou, Rui ;

Zheng, Jun-Cheng ;

Deng, Xian-Ming ;

Sun, Xiu-Li ;

Shen, Qi ;

Tang, Yong .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (10) :3454-3457

[60] Acceptor/Acceptor-Substituted Diazo Reagents for Carbene Transfers: Cobalt-Catalyzed Asymmetric Z-Cyclopropanation of Alkenes with α-Nitrodiazoacetates [J].

Zhu, Shifa ;

Perman, Jason A. ;

Zhang, X. Peter .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (44) :8460-8463

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