Application of O-2-DMSO as reoxidant in the Pd(II)-catalyzed 1,4-oxidation of 5-substituted 1,3-cyclohexadienes

被引：14

作者：

Ronn, M ^{[1
]}

Andersson, PG ^{[1
]}

Backvall, JE ^{[1
]}

机构：

[1] UNIV UPPSALA,DEPT ORGAN CHEM,S-75121 UPPSALA,SWEDEN

来源：

ACTA CHEMICA SCANDINAVICA | 1997年 / 51卷 / 6-7期

关键词：

D O I：

10.3891/acta.chem.scand.51-0773

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Palladium-catalyzed oxidation of 5-substituted 1,3-cyclohexadienes carrying a nucleophilic group in the side chain employing O-2-DMSO as the oxidant gave cyclization via 1,4-addition to the 1,3-diene. The nucleophilic groups employed were tosylamido and carboxy. In the reaction Pd-II is most likely reduced to colloidal Pd-0 which is subsequently reoxidized by O-2. The solvent DMSO prevents precipitation of metallic palladium by coordination to the colloidal particles. The stereochemistry of the palladium-catalyzed intramolecular 1,4-oxidation was controlled to some extent by the nature of the external nucleophile. Thus, in the intramolecular 1,4-oxyacyloxylation of 1 (hydroxy as nucleophile in the side chain) it was possible to direct the 1,4-addition towards cis or trans stereochemistry by variation of the external carboxylate nucleophile.

引用

页码：773 / 777

页数：5

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