New nitrogen containing chiral diselenides: Synthesis and asymmetric addition reactions to olefins

被引:73
作者
Tiecco, M [1 ]
Testaferri, L [1 ]
Santi, C [1 ]
Tomassini, C [1 ]
Marini, F [1 ]
Bagnoli, L [1 ]
Temperini, A [1 ]
机构
[1] Univ Perugia, Dipartimento Chim & Tecnol Farmaco, Sez Chim Organ, I-06123 Perugia, Italy
关键词
D O I
10.1016/S0957-4166(00)00469-9
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A simple synthesis of two new nitrogen containing diselenides, 7 and 8, is described. These compounds were employed as starting materials to effect the asymmetric methoxyselenenylation, the hydroxyselenenylation as well as the cyclofunctionalization of olefins. Starting from 7 all these addition processes occurred with good facial selectivity. Poor results were however obtained with 8. One-pot selenenylation-elimination sequences using catalytic amounts of the diselenide 7 have also been investigated. (C) 2001 Published by Elsevier Science Ltd.
引用
收藏
页码:4645 / 4650
页数:6
相关论文
共 26 条
[1]   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
[2]   New chiral auxiliaries for highly stereoselective asymmetric methoxyselenenylations [J].
Back, TG ;
Moussa, Z .
ORGANIC LETTERS, 2000, 2 (19) :3007-3009
[3]   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
[4]  
FUJITA K, 1995, TETRAHEDRON LETT, V36, P5219
[5]   Design of optically active selenium reagents having a chiral tertiary amino group and their application to asymmetric inter- and intramolecular oxyselenenylations [J].
Fujita, K ;
Murata, K ;
Iwaoka, M ;
Tomoda, S .
TETRAHEDRON, 1997, 53 (06) :2029-2048
[6]   ASYMMETRIC INTRAMOLECULAR SELENOETHERIFICATION AND SELENOLACTONIZATION USING AN OPTICALLY-ACTIVE DIARYL DISELENIDE DERIVED FROM D-MANNITOL [J].
FUJITA, KI ;
MURATA, K ;
IWAOKA, M ;
TOMODA, S .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (16) :1641-1642
[7]   Asymmetric methoxyselenenylation of alkenes with chiral ferrocenylselenium reagents [J].
Fukuzawa, S ;
Takahashi, K ;
Kato, H ;
Yamazaki, H .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (22) :7711-7716
[8]   HIGHLY SELECTIVE ASYMMETRIC INTRAMOLECULAR SELENOCYCLISATION [J].
NISHIBAYASHI, Y ;
SRIVASTAVA, SK ;
TAKADA, H ;
FUKUZAWA, S ;
UEMURA, S .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (22) :2321-2322
[9]   SYNTHESIS OF CHIRAL DIFERROCENYL DISELENIDES AND THEIR APPLICATION TO ASYMMETRIC REACTIONS [J].
NISHIBAYASHI, Y ;
SINGH, JD ;
UEMURA, S ;
FUKUZAWA, S .
TETRAHEDRON LETTERS, 1994, 35 (19) :3115-3118
[10]   RHODIUM(I)-CATALYZED ASYMMETRIC HYDROSILYLATION OF KETONES USING NEW DIFERROCENYL DICHALCOGENIDES (R,S)-([EC(5)H(3)CHME(NME(2))]FE(C5H5))(2) (E=S, SE, TE), AS CHIRAL LIGANDS [J].
NISHIBAYASHI, Y ;
SINGH, JD ;
SEGAWA, K ;
FUKUZAWA, S ;
UEMURA, S .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (11) :1375-1376