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
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.
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页码:609 / 612
页数:4
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