One-step synthesis of α-pyrones from acyl chlorides by the Stille reaction

被引：50
作者：
Thibonnet, J
Abarbri, M
Parrain, JL
Duchêne, A
机构：
[1] Fac Sci & Tech St Jerome, CNRS, UMR 6009, Lab Synth Organ, F-13397 Marseille 20, France
[2] Fac Sci Tours, Lab Physicochim Interfaces & Milieux React, EA 2098, LRC,MO2, F-37200 Tours, France
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 11期
关键词：
D O I：
10.1021/jo025518v
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Palladium-catalyzed stereoselective annulation of a functional vinylstannane by acyl chlorides gives the corresponding alpha-pyran-2-ones in good yields. This annulation most probably proceeds through a Stille reaction/cyclization sequence.
引用
收藏
页码：3941 / 3944
页数：4
相关论文
共 47 条
[11]  
FARINA V, 1996, ADV MET ORG, V5, P1
[12]   STRUCTURE-ACTIVITY-RELATIONSHIPS OF INSECTICIDAL AMIDES FROM PIPER-GUINEENSE ROOT [J].
GBEWONYO, WSK ;
CANDY, DJ ;
ANDERSON, M .
PESTICIDE SCIENCE, 1993, 37 (01) :57-66
[13]   Lewis acid-promoted disproportionation reaction of aromatic vinyl ethers and acetals and its application to the synthesis of paracotoin [J].
Gong, YD ;
Tanaka, H ;
Iwasawa, N ;
Narasaka, K .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1998, 71 (09) :2181-2185
[14]   PELLITORINE ISOMERS .2. THE SYNTHESIS OF N-ISOBUTYL-TRANS-2,TRANS-4-DECADIENAMIDE [J].
JACOBSON, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (11) :2584-2586
[15]   Trail pheromone of myrmicine ant Pristomyrmex pungens [J].
Janssen, E ;
Holldobler, B ;
Kern, F ;
Bestmann, HJ ;
Tsuji, K .
JOURNAL OF CHEMICAL ECOLOGY, 1997, 23 (04) :1025-1034
[16]  
Knight D.W., 1994, CONTEMP ORG SYNTH, V1, P287, DOI DOI 10.1021/CR60230A002
[17]  
KVITA V, 1992, CHIMIA, V46, P457
[18]  
KVITA V, 1993, CHIMIA, V47, P3
[19]   Synthesis of isocoumarins and α-pyrones via palladium-catalyzed annulation of internal alkynes [J].
Larock, RC ;
Doty, MJ ;
Han, XJ .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (24) :8770-8779
[20]   STUDIES IN GROUP 4 ORGANOMETALLIC CHEMISTRY .26. FREE RADICAL TRANS-ADDITION OF ORGANOTIN HYDRIDES TO CARBON-CARBON TRIPLE BONDS [J].
LEUSINK, AJ ;
BUDDING, HA .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1968, 11 (03) :533-&
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