Iridium-catalyzed asymmetric allylic substitution with aryl zinc reagents

被引:71
作者
Alexakis, Alexandre [1 ]
El Hajjaji, Samir [1 ]
Polet, Damien [1 ]
Rathgeb, Xavier [1 ]
机构
[1] Univ Geneva, Dept Chim Organ, CH-1211 Geneva 4, Switzerland
关键词
D O I
10.1021/ol0713842
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Thanks to iridium catalysis, arylzinc reagents undergo regioselective allylic substitution with very high enantioselectivity, when associated with phosphoramidite ligands.
引用
收藏
页码:3393 / 3395
页数:3
相关论文
共 46 条
[1]   The copper-catalyzed asymmetric allylic substitution [J].
Alexakis, A ;
Malan, C ;
Lea, L ;
Tissot-Croset, K ;
Polet, D ;
Falciola, C .
CHIMIA, 2006, 60 (03) :124-130
[2]   Very efficient phosphoramidite ligand for asymmetric iridium-catalyzed allylic alkylation [J].
Alexakis, A ;
Polet, D .
ORGANIC LETTERS, 2004, 6 (20) :3529-3532
[3]  
Bartels B, 2003, EUR J ORG CHEM, V2003, P1097
[4]   ASYMMETRIC-SYNTHESIS IN THE NICKEL-COMPLEX-CATALYZED FORMATION OF OLEFINS FROM ALLYL ALCOHOLS AND GRIGNARD-REAGENTS [J].
CHEREST, M ;
FELKIN, H ;
UMPLEBY, JD ;
DAVIES, SG .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (14) :681-682
[5]   Nickel(0)-catalysed asymmetric cross-coupling reactions of allylic compounds with Grignard reagents using optically active oxazolinylferrocenylphosphines as ligands [J].
Chung, KG ;
Miyake, Y ;
Uemura, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (16) :2725-2729
[6]  
COE BK, 1983, J PHARMACOL EXP THER, V226, P686
[7]   ASYMMETRIC NICKEL-CATALYZED CROSS-COUPLING REACTION OF ALLYLIC SUBSTRATES WITH GRIGNARD-REAGENTS [J].
CONSIGLIO, G ;
PICCOLO, O ;
RONCETTI, L ;
MORANDINI, F .
TETRAHEDRON, 1986, 42 (07) :2043-2053
[8]   ENANTIOSELECTIVE ALLYLATION OF GRIGNARD-REAGENTS WITH NICKEL DIPHOSPHINE CATALYSTS [J].
CONSIGLIO, G ;
INDOLESE, A .
ORGANOMETALLICS, 1991, 10 (10) :3425-3427
[9]   Catalytic asymmetric synthesis of diarylacetates and 4,4-diarylbutanoates. A formal asymmetric synthesis of (+)-sertraline [J].
Davies, HML ;
Stafford, DG ;
Hansen, T .
ORGANIC LETTERS, 1999, 1 (02) :233-236
[10]   Regio- and enantiospecific rhodium-catalyzed arylation of unsymmetrical fluorinated acyclic allylic carbonates: inversion of absolute configuration [J].
Evans, PA ;
Uraguchi, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (24) :7158-7159