A CONVENIENT STEREOSELECTIVE SYNTHESIS OF CONJUGATED (2Z)-EN-4-YNOIC AND (2Z,4Z)-DIENOIC AND (2Z,4E)-DIENOIC ACID-DERIVATIVES FROM PROPIOLIC ACID-DERIVATIVES

被引:36
作者
LU, XY
HUANG, XL
MA, SM
机构
[1] Shanghai Institute of Organic Chemistry, Academia Sinica, Shanghai, 200032
关键词
D O I
10.1016/S0040-4039(00)92235-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The palladium-catalysed one-pot sequential reaction of propiolic acid derivatives with lithium halides first and then with terminal alkynes or alkenes affords conjugated (2Z)-en-4-ynoic and (2Z,4Z)- and (2Z,4E)- dienoic acid derivatives with high stereoselectivity.
引用
收藏
页码:2535 / 2538
页数:4
相关论文
共 29 条
[1]   PALLADIUM-CATALYZED POLYENE CYCLIZATIONS OF DIENYL ARYL IODIDES [J].
ABELMAN, MM ;
OVERMAN, LE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (07) :2328-2329
[2]   INTRAMOLECULAR ALKENE ARYLATIONS FOR RAPID ASSEMBLY OF POLYCYCLIC SYSTEMS CONTAINING QUATERNARY CENTERS - A NEW SYNTHESIS OF SPIROOXINDOLES AND OTHER FUSED AND BRIDGED RING-SYSTEMS [J].
ABELMAN, MM ;
OH, T ;
OVERMAN, LE .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (18) :4130-4133
[3]  
[Anonymous], 1973, NATURALLY OCCURRING
[4]  
BECKSTROM P, 1988, TETRAHEDRON, V44, P2541
[5]   STRUCTURE ACTIVITY STUDIES ON AGGREGATION PHEROMONE COMPONENTS OF PITYOGENES-CHALCOGRAPHUS (COLEOPTERA, SCOLYTIDAE) - ALL STEREOISOMERS OF CHALCOGRAN AND METHYL 2,4-DECADIENOATE [J].
BYERS, JA ;
HOGBERG, HE ;
UNELIUS, CR ;
BIRGERSSON, G ;
LOFQVIST, J .
JOURNAL OF CHEMICAL ECOLOGY, 1989, 15 (02) :685-695
[6]   SYNTHESIS OF ARYL-SUBSTITUTED AND VINYL-SUBSTITUTED ACETYLENE DERIVATIVES BY USE OF NICKEL AND PALLADIUM COMPLEXES [J].
CASSAR, L .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1975, 93 (02) :253-257
[7]  
HECK RF, 1982, ORG REACTIONS, V27, P345
[8]   SELECTIVE PROTON-TRANSFER OF UNSATURATED ESTERS - SYNTHESES OF A TRAIL-FOLLOWING PHEROMONE FOR SUBTERRANEAN TERMITES AND MEGATOMOIC ACID [J].
IKEDA, Y ;
UKAI, J ;
IKEDA, N ;
YAMAMOTO, H .
TETRAHEDRON, 1987, 43 (04) :743-753
[9]   VINYL-COPPER DERIVATIVES .13. SYNTHESIS OF CONJUGATED DIENES OF VERY HIGH STEREOISOMERIC PURITY [J].
JABRI, N ;
ALEXAKIS, A ;
NORMANT, JF .
TETRAHEDRON LETTERS, 1981, 22 (10) :959-962