Stereoselective intramolecular cyclization of allyl and homoallyl benzamide via π-allylpalladium complex catalyzed by Pd(0)

被引：65

作者：

Lee, KY ^{[1
]}

Kim, YH ^{[1
]}

Park, MS ^{[1
]}

Oh, CY ^{[1
]}

Ham, WH ^{[1
]}

机构：

[1] Sungkyunkwan Univ, Coll Pharm, Suwon 440746, South Korea

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 26期

关键词：

D O I：

10.1021/jo991065r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The transformation of acyclic allylic benzamides 4 and homoallylic benzamides 12 to vinyl oxazolines 3 is achieved in the presence of base by the catalysis of Pd(0) in high yield and with high diastereoselectivity. Especially, in the case of homoallylic benzamides 12, trans-oxazolines 3 are formed exclusively or predominantly over cis-oxazolines 8, irrespective of the composition of their stereoisomers. The reaction is believed to proceed via the same pi-allylpalladium complex that arises from either primary or secondary allylic acetates. We applied this method to the syntheses of beta-amino-alpha-hydroxy acids 1 and gamma-amino-beta-hydroxy acids 2, conveniently protected as oxazoline.

引用

页码：9450 / 9458

页数：9

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