Efficient copper-mediated reactions of nitrenes derived from sulfonimidamides

被引:72
作者
Leca, D [1 ]
Toussaint, A [1 ]
Mareau, C [1 ]
Fensterbank, L [1 ]
Lacôte, E [1 ]
Malacria, M [1 ]
机构
[1] Univ Paris 06, Chim Organ Lab, UMR 7611, CNRS, F-75005 Paris, France
关键词
D O I
10.1021/ol0485520
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Sulfonimidamides lead efficiently to nitrenes and have been converted to sulfimides, sulfoximines, and aziridines in good yields, through a copper-mediated multicomponent reaction. The stereogenic sulfur atom and the trivalent nitrogen atom present in the molecules open the way to asymmetric synthesis, whose first results are presented.
引用
收藏
页码:3573 / 3575
页数:3
相关论文
共 36 条
[1]   REACTION OF METHANESULFONYL NITRENE WITH BENZENE - ATTEMPTS TO GENERATE SULFONYL NITRENES FROM SOURCES OTHER THAN AZIDES [J].
ABRAMOVITCH, RA ;
BAILEY, TD ;
TAKAYA, T ;
UMA, V .
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (03) :340-345
[2]   A simple copper catalyst for both aziridination of alkenes and amination of activated hydrocarbons with chloramine-T trihydrate [J].
Albone, DP ;
Aujla, PS ;
Taylor, PC ;
Challenger, S ;
Derrick, AM .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (25) :9569-9571
[3]   Nitrogen atom transfer to alkenes utilizing chloramine-T as a nitrogen source [J].
Ando, T ;
Minakata, S ;
Ryu, I ;
Komatsu, M .
TETRAHEDRON LETTERS, 1998, 39 (3-4) :309-312
[4]  
Bolm C, 1999, SYNTHESIS-STUTTGART, P1251
[5]   Mechanistic studies of copper-catalyzed alkene aziridination [J].
Brandt, P ;
Södergren, MJ ;
Andersson, PG ;
Norrby, PO .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (33) :8013-8020
[6]   Highly diastereoselective conjugate addition to alkylidene Bis(Sulfoxides):: Asymmetric synthesis of (+)-erythro-roccellic acid [J].
Brebion, F ;
Delouvrié, B ;
Nájera, F ;
Fensterbank, L ;
Malacria, M ;
Vaissermann, J .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (43) :5342-5345
[7]   Efficient aziridination of olefins catalyzed by a unique disilver(I) compound [J].
Cui, Y ;
He, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (52) :16202-16203
[8]   Copper-catalyzed nitrogen transfer mediated by iodosylbenzene PhI=O [J].
Dauban, P ;
Sanière, L ;
Tarrade, A ;
Dodd, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (31) :7707-7708
[9]   Asymmetric intramolecular radical vinylation using enantiopure sulfoxides as temporary chiral auxiliaries [J].
Delouvrié, B ;
Fensterbank, L ;
Lacôte, E ;
Malacria, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (49) :11395-11401
[10]   Nitrogen transfer from a nitridomanganese(V) complex: Amination of silyl enol ethers [J].
DuBois, J ;
Hong, J ;
Carreira, EM ;
Day, MW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (04) :915-916