Unique regio- and stereoselectivity in the allylation of benzaldehyde with 2-substituted allylzincs generated by umpolung of π-allylpalladium

被引：27

作者：

Shimizu, M ^{[1
]}

Kimura, M ^{[1
]}

Tanaka, S ^{[1
]}

Tamaru, Y ^{[1
]}

机构：

[1] Nagasaki Univ, Fac Engn, Dept Appl Chem, Nagasaki 852, Japan

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 07期

关键词：

D O I：

10.1016/S0040-4039(97)10657-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

alpha,beta-Disubstituted allylzincs with alkoxycarbonyl as the beta-substituent, generated via an umpolung of in situ generated pi-allylpalladium by transmetallation with diethylzinc, react with benzaldehyde at the most substituted allylic terminus to provide syn-gamma-butyrolactones 4 exclusively, while those with electron-donating Me, i-Pr, or OMOM as the beta-substituents react at both allylic termini to give mixtures of syn-2, anti-2 and Z-3. alpha,beta,gamma-Trisubstituted allylzincs provide Z,anti-adducts 5 exclusively. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：609 / 612

页数：4

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