Morita-Baylis-Hillman reaction and cyclization of 1-(p-toluenesulfonyl)-1,3-butadiene with aldimines

被引：45

作者：

Back, TG ^{[1
]}

Rankic, DA ^{[1
]}

Sorbetti, JM ^{[1
]}

Wulff, JE ^{[1
]}

机构：

[1] Univ Calgary, Dept Chem, Calgary, AB T2N 1N4, Canada

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 12期

关键词：

D O I：

10.1021/ol050658n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aldimines 2 underwent Morita-Baylis-Hillman reaction with 1-(p-toluenesulfonyl)-1,3-butadiene (3) in the presence of 3-hydroxyquinucildine (HOD) to afford adducts 4. The E-isomers of the products cyclized to the corresponding functionalized piperidines 8 under base-catalyzed conditions. Simultaneous equilibration of (E)-4 and (Z)-4 was effected by photoisomerization to improve the efficiency of the cyclization.

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页码：2377 / 2379

页数：3

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