Salen Promoted Enantioselective Nazarov Cyclizations of Activated and Unactivated Dienones

被引：73

作者：

Hutson, Gerri E. ^{[1
]}

Tuerkmen, Yunus E. ^{[1
]}

Rawal, Viresh H. ^{[1
]}

机构：

[1] Univ Chicago, Dept Chem, Chicago, IL 60637 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2013年 / 135卷 / 13期

关键词：

DIELS-ALDER REACTIONS; CATALYSTS; ACIDS;

D O I：

10.1021/ja401908m

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel class of chiral 5,5'-di(2,4,6-trialkyl)-aryl salen-metal complexes have been developed and shown to catalyze highly enantioselective Nazarov cyclization reactions, giving rise to cyclopentenoids in 90:10-98:2 er. Significantly, the catalysts also promote, for the first time, highly enantioselective Nazarov reactions of "unactivated" dienones, producing hydrindenone products having in place three contiguous chiral centers.

引用

收藏

页码：4988 / 4991

页数：4

相关论文

共 44 条

[1] Catalytic enantioselective Pudovik reaction of aldehydes and aldimines with tethered bis(8-quinolinato) (TBOx) aluminum complex [J].

Abell, Joshua P. ;

Yamamoto, Hisashi .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (32) :10521-+

[2] Asymmetric catalysis of carbon-carbon bond-forming reactions using metal(salen) complexes [J].

Achard, TRJ ;

Clutterbuck, LA ;

North, M .

SYNLETT, 2005, (12) :1828-1847

[3] Catalytic asymmetric nazarov reactions promoted by chiral Lewis acid complexes [J].

Aggarwal, VK ;

Beffield, AJ .

ORGANIC LETTERS, 2003, 5 (26) :5075-5078

[4] An Organocatalytic Asymmetric Nazarov Cyclization [J].

Basak, Ashok K. ;

Shimada, Naoyuki ;

Bow, William F. ;

Vicic, David A. ;

Tius, Marcus A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (24) :8266-+

[5] Total synthesis of (±)-terpestacin and (±)-11-epi-terpestacin [J].

Berger, Gideon O. ;

Tius, Marcus A. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (17) :6473-6480

[6] Enamine-Iminium Ion Nazarov Cyclization of α-Ketolenones [J].

Bow, William F. ;

Basak, Ashok K. ;

Jolit, Anais ;

Vicic, David A. ;

Tius, Marcus A. .

ORGANIC LETTERS, 2010, 12 (03) :440-443

[7] Asymmetric Nazarov Reaction Catalyzed by Chiral Tris(oxazoline)/Copper(II) [J].

Cao, Peng ;

Deng, Chao ;

Zhou, You-Yun ;

Sun, Xiu-Li ;

Zheng, Jun-Cheng ;

Xie, Zuowei ;

Tang, Yong .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (26) :4463-4466

[8]

Cozzi P. G., 2004, CHEM REV, V104, P410

[9] The Nazarov cyclization in organic synthesis. Recent advances [J].

Frontier, AJ ;

Collison, C .

TETRAHEDRON, 2005, 61 (32) :7577-7606

[10] Synthesis and Structure Revision of Nakiterpiosin [J].

Gao, Shuanhu ;

Wang, Oiaoling ;

Chen, Chuo .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (04) :1410-+

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