RECENT PROGRESS IN ORGANOCATALYTIC ASYMMETRIC HALOCYCLIZATION

被引:148
作者
Murai, Kenichi [1 ]
Fujioka, Hiromichi [1 ]
机构
[1] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan
关键词
Asymmetric Halocyclization; Organocatalyst; Enantioselective Halolactonization; gamma-Lactone; delta-Lactone; C-3-SYMMETRIC CHIRAL TRISIMIDAZOLINE; ONE-POT SYNTHESIS; ENANTIOSELECTIVE HALOCYCLIZATION; ELECTROPHILIC FLUORINATION; EFFICIENT SYNTHESIS; ANTIFUNGAL LACTONE; ACID-DERIVATIVES; CARBOXYLIC-ACIDS; DOMINO REACTION; C-3; SYMMETRY;
D O I
10.3987/REV-12-762
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In this review, recent progress made in the development of organocatalytic asymmetric halocyclization reactions that form heterocyclic compounds is described. New reactions and their mechanistic features are discussed in the context of an outline based on catalyst types, including biscinchona alkaloids, amino ureas, amino thioureas, amino thiocarbamates, chiral phosphoric acids, and trisimidazolines.
引用
收藏
页码:763 / +
页数:44
相关论文
共 107 条
[11]   Organocatalytic Asymmetric Halogenation/Semipinacol Rearrangement: Highly Efficient Synthesis of Chiral α-Oxa-Quaternary β-Haloketones [J].
Chen, Zhi-Min ;
Zhang, Qing-Wei ;
Chen, Zhi-Hua ;
Li, Hui ;
Tu, Yong-Qiang ;
Zhang, Fu-Min ;
Tian, Jin-Miao .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (23) :8818-8821
[12]   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
[13]   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
[14]   Catalytic, Asymmetric Halofunctionalization of Alkenes-A Critical Perspective [J].
Denmark, Scott E. ;
Kuester, William E. ;
Burk, Matthew T. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (44) :10938-10953
[15]   Enantioselective Bromocycloetherification by Lewis Base/Chiral Bronsted Acid Cooperative Catalysis [J].
Denmark, Scott E. ;
Burk, Matthew T. .
ORGANIC LETTERS, 2012, 14 (01) :256-259
[16]   Lewis base catalysis of bromo- and iodolactonization, and cycloetherification [J].
Denmark, Scott E. ;
Burk, Matthew T. .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2010, 107 (48) :20655-20660
[17]   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-+
[18]   C2-symmetric chiral bis(oxazoline) ligands in asymmetric catalysis [J].
Desimoni, Giovanni ;
Faita, Giuseppe ;
Jorgensen, Karl Anker .
CHEMICAL REVIEWS, 2006, 106 (09) :3561-3651
[19]   Achiral Counterion Control of Enantioselectivity in a Bronsted Acid-Catalyzed Iodolactonization [J].
Dobish, Mark C. ;
Johnston, Jeffrey N. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (14) :6068-6071
[20]   Asymmetric Synthesis of (+)-Tanikolide and the ß-Methyl-Substituted Analogues of (+)-Tanikolide and (-)-Malyngolide [J].
Doran, Robert ;
Duggan, Lesley ;
Singh, Surrendra ;
Duffy, Colm D. ;
Guiry, Patrick J. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (35) :7097-7106