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.
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页码：1967 / 1973
页数：7
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