Cyclopalladated ferrocenyl amines as enantioselective catalysts for the rearrangement of allylic imidates to allylic amides

被引:91
作者
Hollis, TK [1 ]
Overman, LE [1 ]
机构
[1] UNIV CALIF IRVINE,DEPT CHEM,IRVINE,CA 92697
关键词
D O I
10.1016/S0040-4039(97)10385-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first examples of the use of cyclopalladated complexes in enantioselective catalysis are reported. Cyclopalladated ferrocenyl amine Gf promotes the rearrangement of some 2-alkenyl imidates to allylically transposed amides in excellent yield and moderate enantioselectivity. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:8837 / 8840
页数:4
相关论文
共 13 条
[1]   First enantioselective catalyst for the rearrangement of allylic imidates to allylic amides [J].
Calter, M ;
Hollis, TK ;
Overman, LE ;
Ziller, J ;
Zipp, GG .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (05) :1449-1456
[2]  
CANTY AJ, 1995, COMPREHENSIVE ORGA 2, V9, P242
[3]   ELECTROPHILIC AROMATIC SUBSTITUTION REACTIONS BY PLATINUM(2) AND PALLADIUM(2) CHLORIDES ON N,N-DIMETHYLBENZYLAMINES [J].
COPE, AC ;
FRIEDRICH, EC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (04) :909-+
[4]   AN APPRAISAL OF SQUARE-PLANAR SUBSTITUTION-REACTIONS [J].
CROSS, RJ .
ADVANCES IN INORGANIC CHEMISTRY, 1989, 34 :219-292
[5]   Facile interconversions between diastereomers of chloro-bridged palladium(II) dimers of orthometallated (+/-)-dimethyl[1-(1-naphthyl)ethyl]amine [J].
Hockless, DCR ;
Gugger, PA ;
Leung, PH ;
Mayadunne, RC ;
Pabel, M ;
Wild, SB .
TETRAHEDRON, 1997, 53 (11) :4083-4094
[6]  
KUZMINA LG, 1979, IAN SSSR KH, P1528
[7]   Syntheses and characterization of optically active cyclopalladated compounds containing ferrocenyl units. [J].
Lopez, C ;
Bosque, R ;
Solans, X ;
FontBardia, M .
TETRAHEDRON-ASYMMETRY, 1996, 7 (09) :2527-2530
[8]   GENERAL METHOD FOR SYNTHESIS OF AMINES BY REARRANGEMENT OF ALLYLIC TRICHLOROACETIMIDATES - 1,3 TRANSPOSITION OF ALCOHOL AND AMINE FUNCTIONS [J].
OVERMAN, LE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (10) :2901-2910
[9]   Allylic transposition of alcohol and amine functionality by thermal or palladium(II)-catalyzed rearrangements of allylic N-benzoylbenzimidates [J].
Overman, LE ;
Zipp, GG .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (07) :2288-2291
[10]   ALLYLIC AND PROPARGYLIC IMIDIC ESTERS IN ORGANIC-SYNTHESIS [J].
OVERMAN, LE .
ACCOUNTS OF CHEMICAL RESEARCH, 1980, 13 (07) :218-224