Asymmetric Bromolactonization Using Amino-thiocarbamate Catalyst

被引：290

作者：

Zhou, Ling ^{[1
]}

Tan, Chong Kiat ^{[1
]}

Jiang, Xiaojian ^{[1
]}

Chen, Feng ^{[1
]}

Yeung, Ying-Yeung ^{[1
]}

机构：

[1] Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 44期

关键词：

BROMOSUCCINIMIDE; HALOCYCLIZATION; OLEFINS; POTENT;

D O I：

10.1021/ja1048972

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel amino-thiocarbamate-catalyzed bromolactonization of unsaturated carboxylic acids has been developed. The scope of the reaction is evidenced by 22 examples of gamma-lactones with up to 99% yield and 93% ee. The protocol was applied in the enantioselective synthesis of the key intermediates of VLA-4 antagonists.

引用

页码：15474 / 15476

页数：3

共 20 条

[1] Amidines as potent nucleophilic organocatalysts for the transfer of electrophilic bromine from N-bromosuccinimide to alkenes [J].

Ahmad, Simon M. ;

Braddock, D. Christopher ;

Cansell, Gemma ;

Hermitage, Stephen A. ;

Redmond, Joanna M. ;

White, Andrew J. P. .

TETRAHEDRON LETTERS, 2007, 48 (34) :5948-5952

[2] Thiourea catalysis of NCS in the synthesis of chlorohydrins [J].

Bentley, Paul A. ;

Mei, Yujiang ;

Du, Juan .

TETRAHEDRON LETTERS, 2008, 49 (08) :1425-1427

[3] Bromoiodinanes with an I(III)-Br bond: preparation, X-ray crystallography and reactivity as electrophilic brominating agents [J].

Braddock, DC ;

Cansell, G ;

Hermitage, SA ;

White, AJP .

CHEMICAL COMMUNICATIONS, 2006, (13) :1442-1444

[4] Investigation of the early steps in electrophilic bromination through the study of the reaction with sterically encumbered olefins [J].

Brown, RS .

ACCOUNTS OF CHEMICAL RESEARCH, 1997, 30 (03) :131-137

[5] Efficient aziridination of olefins catalyzed by mixed-valent dirhodium(II,III) caprolactamate [J].

Catino, AJ ;

Nichols, JM ;

Forslund, RE ;

Doyle, MP .

ORGANIC LETTERS, 2005, 7 (13) :2787-2790

[6] Aluminium Powder-Catalyzed Regio- and Stereoselective Aminobromination of α,β-Unsaturated Carbonyl Compounds and Simple Olefins with the p-Toluenesulfonamide/N-Bromosuccinimide (TsNH2-NBS) System [J].

Chen, Zhan-Guo ;

Wei, Jun-Fa ;

Wang, Ming-Zhen ;

Zhou, Li-Yan ;

Zhang, Cong-Jie ;

Shi, Xian-Ying .

ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (14-15) :2358-2368

[7] Mechanistic evaluation of the halocyclization of 4-penten-1-ol by some bis(2-substituted pyridine) and bis(2,6-disubstituted pyridine)bromonium triflates [J].

Cui, XL ;

Brown, RS .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (18) :5653-5658

[8] Lewis base activation of lewis acids: Development of a Lewis base catalyzed selenolactonization [J].

Denmark, Scott E. ;

Collins, William R. .

ORGANIC LETTERS, 2007, 9 (19) :3801-3804

[9] On the Absolute Configurational Stability of Bromonium and Chloronium Ions [J].

Denmark, Scott E. ;

Burk, Matthew T. ;

Hoover, Andrew J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (04) :1232-+

[10] Substituted tetrahydrofuroyl-1-phenylalanine derivatives as potent and specific VLA-4 antagonists [J].

Doherty, GA ;

Yang, GX ;

Borges, E ;

Chang, LL ;

MacCoss, M ;

Tong, S ;

Kidambi, U ;

Egger, LA ;

McCauley, E ;

Van Riper, G ;

Mumford, RA ;

Schmidt, JA ;

Hagmann, WK .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (11) :1501-1505

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