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
收藏
页码：773 / 777
页数：5
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