Organocatalyzed Enantioselective Fluorocyclizations

被引：319

作者：

Lozano, Oscar ^{[1
]}

Blessley, George ^{[1
]}

del Campo, Teresa Martinez ^{[1
]}

Thompson, Amber L. ^{[1
]}

Giuffredi, Guy T. ^{[1
]}

Bettati, Michela ^{[2
]}

Walker, Matthew ^{[2
]}

Borman, Richard ^{[2
]}

Gouverneur, Veronique ^{[1
]}

机构：

[1] Univ Oxford, Chem Res Lab, 12 Mansfield Rd, Oxford OX1 3TA, England

[2] GlaxoSmithKline R&D, Stevenage SG1 2NY, Herts, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 35期

关键词：

alkaloids; asymmetric catalysis; fluorocyclizations; indoles; organocatalysis; ASYMMETRIC IODOCYCLIZATION; FLUORINATION; IODOCARBOCYCLIZATION; HALOCYCLIZATION; BROMOLACTONIZATION; IODOLACTONIZATION; COMPLEXES;

D O I：

10.1002/anie.201103151

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Enantioenriched fluorinated heterocycles can be prepared through fluorocyclizations of prochiral indoles (see scheme; Ts=tosyl, Bn=benzyl, Boc=tert-butoxycarbonyl). More than twenty examples for this cascade fluorination-cyclization, which is catalyzed by cinchona alkaloids and employs N-fluorobenzenesulfonimide as the electrophilic fluorine source have been explored, and an unprecedented catalytic asymmetric difluorocyclization has also been identified. © 2011 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：8105 / 8109

页数：5

共 55 条

[51] An Organocatalytic Asymmetric Chlorolactonization [J].

Whitehead, Daniel C. ;

Yousefi, Roozbeh ;

Jaganathan, Arvind ;

Borhan, Babak .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (10) :3298-+

[52] Developments in fluorocyclization methodologies [J].

Wilkinson, Susan C. ;

Salmon, Roger ;

Gouverneur, Veronique .

FUTURE MEDICINAL CHEMISTRY, 2009, 1 (05) :847-863

[53] Electrophilic Fluorocyclization of Allyl Silanes [J].

Wilkinson, Susan C. ;

Lozano, Oscar ;

Schuler, Marie ;

Pacheco, Maria C. ;

Salmon, Roger ;

Gouverneur, Veronique .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (38) :7083-7086

[54] Enantioselective Bromolactonization of Conjugated (Z)-Enynes [J].

Zhang, Wei ;

Zheng, Suqing ;

Liu, Na ;

Werness, Jenny B. ;

Guzei, Ilia A. ;

Tang, Weiping .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (11) :3664-+

[55] Asymmetric Bromolactonization Using Amino-thiocarbamate Catalyst [J].

Zhou, Ling ;

Tan, Chong Kiat ;

Jiang, Xiaojian ;

Chen, Feng ;

Yeung, Ying-Yeung .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (44) :15474-15476

← 1 2 3 4 5 6 →