Stereoselective OsO4-Catalyzed Oxidative Cyclization of 1,5-Dienes

被引：10

作者：

Poethig, Alexander ^{[1
]}

Strassner, Thomas ^{[1
]}

机构：

[1] Tech Univ Dresden, D-01062 Dresden, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 06期

关键词：

OSMIUM-CATALYZED DIHYDROXYLATION; MOLECULAR-ORBITAL METHODS; DENSITY-FUNCTIONAL THEORY; PERMANGANATE OXIDATION; BASIS-SETS; ANNONACEOUS ACETOGENINS; MECHANISM; TETRAHYDROFURAN; INTERMEDIATE; TETROXIDE;

D O I：

10.1021/jo100147e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The mechanism of the oxidation of 1,5-dienes with osmium tetroxide was investigated by density functional theory calculations (B3LYP/6-311+G*). The observed products, 2,5-bis(hydroxymethyl)tetrahydrofurans, are formed stereoselectively in it concerted reaction. Enantioselectivity could be induced by an enantioselective dihydroxylation followed by condensation of the 5,6-dihydroxyole-fine with osmium tetroxide, while the diastereoselectivity is achieved by reaction of the 1,5-diene with osmium tetroxide and intermediate reoxidation of the osmium(VI) ester.

引用

页码：1967 / 1973

页数：7

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