SYNTHESIS OF VARIOUSLY 2-SUBSTITUTED ALKYL (Z)-2-ALKENOATE AND (E)-2-ALKENOATE AND (Z)-ALPHA-YLIDENE-GAMMA-BUTYROLACTONE AND (E)-ALPHA-YLIDENE-GAMMA-BUTYROLACTONE VIA PALLADIUM-MEDIATED CROSS-COUPLING REACTIONS BETWEEN ORGANOSTANNANES AND ORGANIC HALIDES

被引:46
作者
BELLINA, F [1 ]
CARPITA, A [1 ]
DESANTIS, M [1 ]
ROSSI, R [1 ]
机构
[1] UNIV PISA,DIPARTIMENTO CHIM & CHIM IND,I-56126 PISA,ITALY
关键词
D O I
10.1016/S0040-4020(01)89314-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Stereoisomerically pure trisubstituted alpha,beta-unsaturated esters of general formula 7 have been efficiently synthetized using two different protocols. The first one involves the palladium(0)/copper(I)-mediated cross-coupling reaction between alkyl (E)-2-tributylstannyl-2-alkenoates, (E)-2, and aryl or alkenyl iodides. The second protocol, which allows to prepare stereodefined 2-aryl, 2-methyl, 2-(1-alkenyl) as well as 2-acyl substituted alpha,beta-unsaturated esters, is based on the cross-coupling reaction between easily available alkyl (Z)- or (E)-2-halo-2-alkenoates and organostannanes in NMP, in the presence of catalytic amounts of PdCl2(PhCN)(2), AsPh(3) and CuI. (Z)-and (E)-2-ethenyl substituted alpha,beta-unsaturated esters prepared according to this procedure have been proven to be useful precursors to (Z)- and (E)-alpha-ylidene-gamma-butyrolactones, (Z)- and (E)-8, respectively.
引用
收藏
页码:12029 / 12046
页数:18
相关论文
共 55 条
[1]   EVIDENCE OF THE FORMATION OF ZEROVALENT PALLADIUM FROM PD(OAC)2 AND TRIPHENYLPHOSPHINE [J].
AMATORE, C ;
JUTAND, A ;
MBARKI, MA .
ORGANOMETALLICS, 1992, 11 (09) :3009-3013
[2]  
[Anonymous], 1977, WILEY ONLINE LIB
[3]  
ARORA AS, METHODEN ORGANISCHEN, V5, P728
[4]  
BACK TG, 1977, TETRAHEDRON LETT, P2651
[5]   NEW SYNTHETIC APPLICATIONS OF ORGANOTIN COMPOUNDS - SYNTHESIS OF STEREODEFINED 2-IODO-2-ALKENONES, 2-SUBSTITUTED (E)-2-ALKENONES AND 2-METHYL-2-CYCLOALKENONES [J].
BELLINA, F ;
CARPITA, A ;
CIUCCI, D ;
DESANTIS, M ;
ROSSI, R .
TETRAHEDRON, 1993, 49 (21) :4677-4698
[6]   REGIOSELECTIVE AND STEREOSELECTIVE SYNTHESIS OF (E)-2-METHYL-1-ALKENYLTRIMETHYLSTANNANES FROM 1-ALKYNES [J].
BELLINA, F ;
CARPITA, A ;
FONTANA, EA ;
ROSSI, R .
TETRAHEDRON, 1994, 50 (17) :5189-5202
[7]  
BELLINA F, IN PRESS TETRAHEDRON
[8]  
CARPITA A, 1987, GAZZ CHIM ITAL, V117, P481
[9]   A NEW ROUTE TO Z-DISUBSTITUTED OLEFINS - A SIMPLE SYNTHESIS OF POLY-UNSATURATED FATTY-ACIDS BY REITERATIVE COUPLING [J].
COREY, EJ ;
ECKRICH, TM .
TETRAHEDRON LETTERS, 1984, 25 (23) :2419-2422
[10]  
Coulson DR, 1971, INORG SYN, V13, P121, DOI DOI 10.1002/9780470132449.CH23