ORGN 561 |
| The catalytic isomerization of allylic alcohols is a useful synthetic method, especially in cases where one allylic alcohol is more challenging to prepare than its isomer. Ongoing studies in these laboratories have revealed that triphenylsilyl perrhennate can rapidly isomerize a wide variety of allylic alcohols. Depending on the reaction conditions, high product selectivity for the formation of primary, secondary and tertiary allylic alcohols can be obtained. Two strategies have been identified for obtaining high product selectivity: the use of substrates bearing conjugating subtituents and the selective silylation of a single isomer with bis-N,O-trimethylsilylacetamide (BTMSA) during the course of the isomerization. The method has been extended to the isomerization of enantioenriched allylic alcohols. Secondary and tertiary allylic alcohols can be obtained with high levels of enantioenrichment.
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Physical Organic Chemistry, Metal-Mediated Reactions, Asymmetric Reactions and Syntheses
8:00 PM-10:00 PM, Tuesday, August 21, 2007 BCEC -- Exhibit Hall - B2, Poster
Division of Organic Chemistry |
