STEREOSELECTIVE REACTIONS OF ALPHA-IMIDE SUBSTITUTED RADICALS

被引：19

作者：

DAMM, W ^{[1
]}

HOFFMANN, U ^{[1
]}

MACKO, L ^{[1
]}

NEUBURGER, M ^{[1
]}

ZEHNDER, M ^{[1
]}

GIESE, B ^{[1
]}

机构：

[1] UNIV BASEL,DEPT CHEM,CH-4056 BASEL,SWITZERLAND

来源：

TETRAHEDRON | 1994年 / 50卷 / 24期

关键词：

D O I：

10.1016/S0040-4020(01)85232-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Barton esters 17 and 18, synthesized from the corresponding amino acid derivatives 6 and 14, were irradiated in situ with or without an external trap. Thus, thiopyridines 22 and 23, phenylselenides 24 and 25, esters 26 and 27 as well as deuterated products 34 and 35 were isolated when the radical 20 and 21 were trapped with Barton esters 17 and 18 or with PhSeSePh, methyl acrylate or Bu(3)SnD. In all cases the anti isomers were isolated as the major products in moderate to excellent selectivity. The stereochemical course of the radical reactions can be explained by the allylic strain model.

引用

页码：7029 / 7048

页数：20

共 22 条

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