Catalytic addition-elimination reactions towards butenolides

被引:23
作者
Brown, Danielle M. [1 ]
Niyomura, Osamu [1 ]
Wirth, Thomas [1 ]
机构
[1] Cardiff Univ, Sch Chem, Cardiff CF10 3AT, Wales
关键词
butenolides; diselenides; selenium electrophiles; stereoselective synthesis;
D O I
10.1080/10426500801901053
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A wide range of selenium-containing reagents are known to undergo addition - elimination reactions under different reaction conditions. We report on selenium electrophiles, which are regenerated under the reaction conditions employed, and therefore only catalytic amounts of these reagents are necessary.
引用
收藏
页码:1026 / 1035
页数:10
相关论文
共 20 条
[11]   Electrochemical generation and catalytic use of selenium electrophiles [J].
Niyomura, O ;
Cox, M ;
Wirth, T .
SYNLETT, 2006, (02) :251-254
[12]   A convergent asymmetric synthesis of γ-butenolides [J].
Renard, M ;
Ghosez, LA .
TETRAHEDRON, 2001, 57 (13) :2597-2608
[13]   POLYSTYRENE-BOUND PHENYLSELENIC ACID - CATALYTIC OXIDATIONS OF OLEFINS, KETONES, AND AROMATIC SYSTEMS [J].
TAYLOR, RT ;
FLOOD, LA .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (26) :5160-5164
[14]   CATALYTIC CONVERSION OF BETA,GAMMA-UNSATURATED ESTERS, AMIDES AND NITRILES INTO GAMMA-ALKOXY OR GAMMA-HYDROXY ALPHA,BETA-UNSATURATED DERIVATIVES INDUCED BY PERSULFATE ANION OXIDATION OF DIPHENYL DISELENIDE [J].
TIECCO, M ;
TESTAFERRI, L ;
TINGOLI, M ;
BAGNOLI, L ;
SANTI, C .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (07) :637-639
[15]  
TIECCO M, 1993, SYNLETT, P798
[16]  
Tiecco M, 1999, EUR J ORG CHEM, V1999, P797
[17]   GENERATION AND RECYCLE USE OF SELENENYLATING REAGENTS IN ELECTROCHEMICAL OXYSELENENYLATION-DESELENENYLATION OF OLEFINS [J].
TORII, S ;
UNEYAMA, K ;
ONO, M ;
BANNOU, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (15) :4606-4608
[18]   ALLYLIC OXIDATION OF OLEFINS BY CATALYTIC AND STOICHIOMETRIC SELENIUM DIOXIDE WITH TERT-BUTYL HYDROPEROXIDE [J].
UMBREIT, MA ;
SHARPLESS, KB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (16) :5526-5528
[19]   Catalytic asymmetric oxyselenenylation-elimination reactions using chiral selenium compounds [J].
Wirth, T ;
Häuptli, S ;
Leuenberger, M .
TETRAHEDRON-ASYMMETRY, 1998, 9 (04) :547-550
[20]  
WIRTH T, 2000, TOP CURR CHEM, V208