Organocatalytic asymmetric α-bromination of aldehydes and ketones

被引:95
作者
Bertelsen, S [1 ]
Halland, N [1 ]
Bachmann, S [1 ]
Marigo, M [1 ]
Braunton, A [1 ]
Jorgensen, KA [1 ]
机构
[1] Aarhus Univ, Dept Chem, Ctr Catalysis, Danish Natl Res Fdn, DK-8000 Aarhus, Denmark
关键词
D O I
10.1039/b509366j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The first organocatalytic enantioselective alpha-bromination of aldehydes and ketones is presented; a C-2-symmetric diphenylpyrrolidine catalyst afforded the alpha-brominated aldehydes in good yields and up to 96% ee, while ketones were alpha-brominated by a C-2-symmetric imidazolidine in up to 94% ee; furthermore, the organocatalytic enantioselective alpha-iodination of aldehydes is also demonstrated to proceed with up to 89% ee.
引用
收藏
页码:4821 / 4823
页数:3
相关论文
共 32 条
[1]  
[Anonymous], 2004, METAL FREE ORGANIC C
[2]   Preparation of enantiomerically enriched bromohydrins from [N-(p-tolylsulfonyl)sulfoximino]oxiranes using in situ reduction of α-bromo aldehydes [J].
Bailey, PL ;
Briggs, AD ;
Jackson, RFW ;
Pietruszka, J .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (20) :3359-3363
[3]   Enantioselective organocatalytic α-fluorination of aldehydes [J].
Beeson, TD ;
MacMillan, DWC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (24) :8826-8828
[4]   Enantioselective chlorination and fluorination of β-keto phosphonates catalyzed by chiral Lewis acids [J].
Bernardi, L ;
Jorgensen, KA .
CHEMICAL COMMUNICATIONS, 2005, (10) :1324-1326
[5]   Direct and enantioselective organocatalytic α-chlorination of aldehydes [J].
Brochu, MP ;
Brown, SP ;
MacMillan, DWC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (13) :4108-4109
[6]   In the golden age of organocatalysis [J].
Dalko, PI ;
Moisan, L .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) :5138-5175
[7]   Direct organocatalytic α-fluorination of aldehydes and ketones [J].
Enders, D ;
Hüttl, MRM .
SYNLETT, 2005, (06) :991-993
[8]   Recent developments in catalytic, asymmetric α-halogenation:: A new frontier in asymmetric catalysis [J].
France, S ;
Weatherwax, A ;
Lectka, T .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (03) :475-479
[9]   Catalytic, asymmetric α-chlorination of acid halides [J].
France, S ;
Wack, H ;
Taggi, AE ;
Hafez, AM ;
Wagerle, TR ;
Shah, MH ;
Dusich, CL ;
Lectka, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (13) :4245-4255
[10]   Direct organocatalytic asymmetric α-chlorination of aldehydes [J].
Halland, N ;
Braunton, A ;
Bachmann, S ;
Marigo, M ;
Jorgensen, KA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (15) :4790-4791