Directed Pd(0)-catalyzed hydrostannations of internal alkynes

被引:16
作者
Marshall, JA [1 ]
Bourbeau, MP [1 ]
机构
[1] Univ Virginia, Dept Chem, Charlottesville, VA 22904 USA
关键词
hydrostannation; vinylstannae; poyketide; directing effects;
D O I
10.1016/S0040-4039(02)02660-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Hydrostannations, of primary propargylic alcohols with Bu3SnH catalyzed by Pd(PPh3)(2) yield (E) allylic alcohols in which the Bu3Sn group is affixed to the carbon proximal to the CH2OH substituent, suggestive of an OH directing effect. Hydrostannations of the related propargylic acetates show no such effect. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1087 / 1089
页数:3
相关论文
共 15 条
[1]   Stereoselective synthesis of functionalized trisubstituted olefins via palladium(0)-catalyzed cross-coupling reaction [J].
Arefolov, A ;
Langille, NF ;
Panek, JS .
ORGANIC LETTERS, 2001, 3 (21) :3281-3284
[2]  
BACKVALL JE, 1983, ORGANOMETALLICS, V2, P1625
[3]   Radical hydrostannylation, Pd(0)-catalyzed hydrostannylation, stannylcupration of propargyl alcohols and enynols: Regio- and stereoselectivities [J].
Betzer, JF ;
Delaloge, F ;
Muller, B ;
Pancrazi, A ;
Prunet, J .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (22) :7768-7780
[4]  
FARINA V, 1997, STILLE REACTION ORGA, P1
[5]  
GREEVES N, 1994, SYNLETT, P537
[6]   Second-generation synthesis of the polypropionate subunit of callystatin a based on regioselective internal alkyne hydrostannation [J].
Marshall, JA ;
Bourbeau, MP .
ORGANIC LETTERS, 2002, 4 (22) :3931-3934
[7]   A new synthesis of 3-carboxy-2,5-disubstituted furans and their conversion to 5-vinyl derivatives [J].
Marshall, JA ;
Zou, D .
TETRAHEDRON LETTERS, 2000, 41 (09) :1347-1350
[8]  
MARSHALL JA, 2002, ORGANOTIN CHEM ORGAN, P377
[9]   PALLADIUM(0) CATALYZED HYDROSTANNYLATION OF ALKYNES - STEREOSPECIFIC SYN ADDITION OF TRIBUTYLTIN HYDRIDE [J].
MIYAKE, H ;
YAMAMURA, K .
CHEMISTRY LETTERS, 1989, (06) :981-984
[10]  
OLSSON LI, 1974, TETRAHEDRON LETT, P2161