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
[11]  
Rice MB, 2001, SYNTHESIS-STUTTGART, P1495
[12]   REGIOCONTROLLED HYDRATION OF 2-BUTYNE-1,4-DIOL DERIVATIVES TO GIVE 4,5-DIHYDRO-3(2H)-FURANONES - PRACTICAL SYNTHESIS OF BULLATENONE AND GEIPARVARIN [J].
SAIMOTO, H ;
HIYAMA, T ;
NOZAKI, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (16) :4975-4977
[13]   NICKEL-CATALYZED CONJUGATE ADDITION OF ALKENYL ZIRCONIUM SPECIES TO ALPHA,BETA-UNSATURATED KETONES [J].
SCHWARTZ, J ;
LOOTS, MJ ;
KOSUGI, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (04) :1333-1340
[14]   Total synthesis of (+)-phorboxazole A exploiting the Petasis-Ferrier rearrangement [J].
Smith, AB ;
Minbiole, KP ;
Verhoest, PR ;
Schelhaas, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (44) :10942-10953
[15]   PALLADIUM-CATALYZED AND MOLYBDENUM-CATALYZED HYDROSTANNATION OF ALKYNES - A NOVEL ACCESS TO REGIODEFINED AND STEREODEFINED VINYLSTANNANES [J].
ZHANG, HX ;
GUIBE, F ;
BALAVOINE, G .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (06) :1857-1867