Pd(0)-catalyzed addition of Me(3)SnSnMe(3) to alpha,beta-alkynic aldehydes and ketones. Synthesis of (Z)-beta-trimethylstannyl alpha,beta-alkenic aldehydes and ketones. Preparation and synthetic uses of substituted (Z)-4-trimethylstannyl-1,3-butadienes

被引:11
作者
Piers, E
Tillyer, RD
机构
[1] Department of Chemistry, University of British Columbia, University Campus, Vancouver
来源
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE | 1996年 / 74卷 / 11期
关键词
Diels-Alder cycloaddition; organocopper(I); transmetallation; alkylidenecyclobutane; (E)-4-lithio-1,3-butadienes; spiro[3.5]nonane;
D O I
10.1139/v96-234
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Treatment (dry tetrahydrofuran, reflux) of the alpha,beta-alkynic aldehydes 26-28 and ketones 29-36 with Me(3)SnSnMe(3) in the presence of a catalytic amount of (Ph(3)P)(4)Pd provides fair to excellent yields of the corresponding (Z)-beta-trimethylstannyl alpha,beta-alkenic aldehydes 41-43 and ketones 44-51. The carbonyl compounds 41-51, upon reaction with methylenetriphenylphosphorane under suitable conditions, are smoothly converted into the (Z)-4-trimethylstannyl-1,3-butadienes 61-71, respectively. Treatment of the aldehyde 41 with the anion of trimethyl phosphonoacetate and the aldehyde 42 with the anion of the phosphonoacetate 73 produces excellent yields of the 5-trimethylstannyl-2,4-heptadienoates 72 and 74, respectively. The synthetic potential of (Z)-4-trimethylstannyl-1,3-butadienes is illustrated by the conversion of 62 into the functionalized, stereodefined conjugated dienes 76 and 78 and by transformation of 87 into the structurally novel diene 84. Diels-Alder reactions of 84 with tetracyanoethylene and dimethyl acetylenedicarboxylate provide the spiro[3.5]nonane derivatives 88 and 89, respectively.
引用
收藏
页码:2048 / 2063
页数:16
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