ORGN 922 |
| Treatment of benzyl 1-phenyl-4,5-hexadienylcarbamate with a catalytic 1:1 mixture of Au[P(t-Bu)2o-biphenyl]Cl and AgOTf (5 mol%) in dioxane at room temperature for 1.25 h led to isolation of benzyl 2-phenyl-5-vinylpyrrolidine-1-carboxylate in 80%yield as a 16:1 mixture of diastereomers. The protocol tolerated substitution at the internal and terminal allenyl carbon atoms as well as substitution at the allenic and homoallenic carbon atoms. The protocol was also effective for the hydroamination of Boc and Fmoc-substituted allenyl carbamates and for the formation of piperidine derivatives.
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Heterocycles and Aromatics
1:00 PM-4:40 PM, Thursday, 14 September 2006 Moscone Center -- Room 135, Oral
Division of Organic Chemistry |
