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
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
[21]   Pd(0)/Ag+-cocatalyzed cyclization reaction of 1,2-allenic carboxylic acids with aryl/alkenyl halides.: An efficient synthesis of butenolides [J].
Ma, SM ;
Shi, ZJ .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (18) :6387-6389
[22]   A NEW SYNTHETIC METHOD FOR PELLITORINE [J].
MANDAI, T ;
GOTOH, J ;
OTERA, J ;
KAWADA, M .
CHEMISTRY LETTERS, 1980, (03) :313-314
[23]   Amination, aminocarbonylation, and alkoxycarbonylation of allenic/propargylic Pd intermediates derived from nonracemic propargylic mesylates: Synthesis of nonracemic propargyl amines, allenic amides, and butenolides [J].
Marshall, JA ;
Wolf, MA .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (10) :3238-3239
[24]   Synthetic routes to allenic acids and esters and their stereospecific conversion to butenolides [J].
Marshall, JA ;
Wolf, MA ;
Wallace, EM .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (02) :367-371
[25]   TOTAL SYNTHESIS OF THE PSEUDOPTERANE (+/-)-KALLOLIDE-B [J].
MARSHALL, JA ;
WALLACE, EM ;
COAN, PS .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (04) :796-797
[26]  
MITCHELL TN, 1992, SYNTHESIS-STUTTGART, P803
[27]   PYROLYSIS OF SULFOXIDE .3. CONVERSION OF 2-(PHENYLSULFINYL)ENOATE TO 2,4-DIENOATE AND SYNTHESIS OF PELLITORINE [J].
NOKAMI, J ;
NISHIUCHI, K ;
WAKABAYASHI, S ;
OKAWARA, R .
TETRAHEDRON LETTERS, 1980, 21 (46) :4455-4456
[28]  
OGAWA Y, 1995, SYNLETT, P871
[29]  
OGAWA Y, 1995, HETEROCYCLES, V41, P2587
[30]  
OMINAGA Y, 1987, J HETEROCYCLIC CHEM, V24, P1557