ORGN 187 |
| Treatment of 2,2-diphenylhexa-4,5-dien-1-ol with a catalytic 1:1 mixture of AuCl[P(t-Bu)2o-biphenyl] and AgOTs at room temperature in toluene for 5 min led to isolation of 4,4-diphenyl-2-vinyl-tetrahydrofuran in 91% yield. The reaction displayed high diastereoselectivity and tolerated substitution at the C1, C2 or C4-carbon atoms of the 5,6-heptadienyl chain and at the terminal allenyl carbon. Allenyl alcohols that possess an axially chiral allenyl moiety underwent cyclization with transfer of chirality from the allene to the newly formed stereogenic tetrahedral carbon atom.
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Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Combinatorial, Parallel, and Solid-Phase Chemistry
8:00 PM-10:00 PM, Sunday, 10 September 2006 Moscone Center -- Hall D, Poster
Division of Organic Chemistry |
