NUCLEOPHILIC-ATTACK AT THE CENTRAL CARBON-ATOM OF (PI-ALLYL)PALLADIUM COMPLEXES - FORMATION OF ALPHA-CYCLOPROPYL ESTERS

被引:70
作者
HOFFMANN, HMR
OTTE, AR
WILDE, A
机构
[1] Institut Für Organische Chemie, Universität Hannover, D-W-3000
来源
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1992年 / 31卷 / 02期
关键词
D O I
10.1002/anie.199202341
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Distinctly higher yields of functionalized cyclopropanes such as 1 can be achieved when 1,2-bis(dimethylamino)ethane, followed by CO, are added to the reaction of pi-allylpalladium complexes with lithium enolates of esters. The usual, energetically favored allylic alkylation is efficiently suppressed in this way. The role of the amine ligands is crucial: addition of 1,2-bis(dimethylamino)methane produces no cyclopropanation product; with sparteine only low yields are obtained.
引用
收藏
页码:234 / 236
页数:3
相关论文
共 13 条
[1]   THE REGIOSELECTIVITIES AND STEREOSELECTIVITIES OF THE REACTION OF ALLYL ACETATES AND SILYL KETENE ACETALS CATALYZED BY PD(0) COMPLEXES - A NEW ROUTE TO CYCLOPROPANE DERIVATIVES [J].
CARFAGNA, C ;
MARIANI, L ;
MUSCO, A ;
SALLESE, G ;
SANTI, R .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (12) :3924-3927
[2]   A MOLECULAR-ORBITAL ANALYSIS OF THE REGIOSELECTIVITY OF NUCLEOPHILIC-ADDITION TO ETA-3-ALLYL COMPLEXES AND THE CONFORMATION OF THE ETA-3-ALLYL LIGAND IN L3(CO)2(ETA-3-C3H5)MOII COMPLEXES [J].
CURTIS, MD ;
EISENSTEIN, O .
ORGANOMETALLICS, 1984, 3 (06) :887-895
[3]   NUCLEOPHILIC-ADDITION TO ORGANOTRANSITION METAL-CATIONS CONTAINING UNSATURATED HYDROCARBON LIGANDS - SURVEY AND INTERPRETATION [J].
DAVIES, SG ;
GREEN, MLH ;
MINGOS, DMP .
TETRAHEDRON, 1978, 34 (20) :3047-3077
[4]  
DAVIES SG, 1986, REACTIONS COORDINATE, V1, P897
[5]   CYCLOPROPANATION OF ESTER ENOLATES BY PI-ALLYLPALLADIUM CHLORIDE COMPLEXES [J].
HEGEDUS, LS ;
DARLINGTON, WH ;
RUSSELL, CE .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (25) :5193-5196
[6]   The Hydroxylation of the double bond [J].
Milas, NA ;
Sussman, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1936, 58 :1302-1304
[7]   NUCLEOPHILIC-ADDITION OF ENOLATES TO THE CENTRAL CARBON OF TRANSITION-METAL ETA-3-ALLYL COMPLEXES - METALLACYCLOBUTANE FORMATION, REVERSIBILITY OF NUCLEOPHILIC-ADDITION, AND SYNTHESIS OF ALPHA-CYCLOPROPYL KETONES [J].
TJADEN, EB ;
STRYKER, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (17) :6420-6422
[8]  
Trost B. M., 1989, ANGEW CHEM, V101, P1199
[9]  
Trost B.M., 1982, COMPREHENSIVE ORGANO, V8, P799, DOI DOI 10.1016/B978-008046518-0.00121-5
[10]   CYCLIZATIONS VIA PALLADIUM-CATALYZED ALLYLIC ALKYLATIONS [J].
TROST, BM .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (09) :1173-1192