Asymmetric methoxyselenenylations with camphor-based selenium electrophiles

被引:29
作者
Back, TG [1 ]
Nan, S [1 ]
机构
[1] Univ Calgary, Dept Chem, Calgary, AB T2N 1N4, Canada
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1998年 / 19期
关键词
D O I
10.1039/a806707d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The asymmetric methoxyselenenylation of olefins was achieved with a series of camphor-based selenenyl triflates, of which the readily available 2-oxo analog 2a proved the most effective.
引用
收藏
页码:3123 / 3124
页数:2
相关论文
共 23 条
[1]  
Back T. G., 1987, ORGANOSELENIUM CHEM
[2]   Asymmetric cyclization of unsaturated alcohols and carboxylic acids with camphor-based selenium electrophiles [J].
Back, TG ;
Dyck, BP .
CHEMICAL COMMUNICATIONS, 1996, (22) :2567-2568
[3]   UNEXPECTED FORMATION OF 1,3-DISELENETANES FROM THE REACTION OF CAMPHOR ENOLATE WITH SELENIUM [J].
BACK, TG ;
DYCK, BP ;
PARVEZ, M .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (04) :515-516
[4]   1,3-DISELENETANES AND 1,3-DITHIETANES DERIVED FROM CAMPHOR - FORMATION, STRUCTURE, STEREOCHEMISTRY, AND OXIDATION TO SELENOXIDE AND SULFOXIDE PRODUCTS [J].
BACK, TG ;
DYCK, BP ;
PARVEZ, M .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (03) :703-710
[5]   A novel camphor-derived selenenamide that acts as a glutathione peroxidase mimetic [J].
Back, TG ;
Dyck, BP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (09) :2079-2083
[6]   ORGANIC TELLURIUM AND SELENIUM CHEMISTRY - REDUCTION OF TELLURIDES, SELENIDES, AND SELENOACETALS WITH TRIPHENYLTIN HYDRIDE [J].
CLIVE, DLJ ;
CHITTATTU, GJ ;
FARINA, V ;
KIEL, WA ;
MENCHEN, SM ;
RUSSELL, CG ;
SINGH, A ;
WONG, CK ;
CURTIS, NJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (13) :4438-4447
[7]   2,6-bis[(2S)-tetrahydrofuran-2-yl]phenyl diselenide: An effective reagent for asymmetric electrophilic addition reactions to olefins [J].
Deziel, R ;
Malenfant, E ;
Thibault, C ;
Frechette, S ;
Gravel, M .
TETRAHEDRON LETTERS, 1997, 38 (27) :4753-4756
[8]   ASYMMETRIC SELENOMETHOXYLATION OF OLEFINS INVOLVING A CHIRAL C2 SYMMETRICAL ELECTROPHILIC ORGANOSELENIUM REAGENT [J].
DEZIEL, R ;
GOULET, S ;
GRENIER, L ;
BORDELEAU, J ;
BERNIER, J .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (14) :3619-3621
[9]  
DYCK BP, 1996, THESIS U CALGARY
[10]   SYNTHESIS OF DIARYL DISELENIDES HAVING CHIRAL PYRROLIDINE RINGS WITH C-2 SYMMETRY - THEIR APPLICATION TO THE ASYMMETRIC METHOXYSELENENYLATION OF TRANS-BETA-METHYLSTYRENES [J].
FUJITA, K ;
IWAOKA, M ;
TOMODA, S .
CHEMISTRY LETTERS, 1994, (05) :923-926