Synthesis of cis-2,5-disubstituted pyrrolidines via diastereoselective reduction of N-acyl iminium ions |
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| Authors: | Alexander C Rudolph |
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| Affiliation: | Department of Chemistry and Biochemistry, The University of Texas, Austin, TX 78712, USA |
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| Abstract: | A new procedure for forming cis-2,5-disubstituted pyrrolidines having unsaturated side chains has been developed that features the diastereoselective reduction of N-acyl iminium ions, which were formed in situ by acid-catalyzed cyclizations of unsaturated γ-keto carbamates, with triphenylsilane. The sequence was applied to a very concise synthesis of 16, a subunit in the nonpeptide cholecystokinin antagonist (+)-RP-66803. |
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| Keywords: | N-Acyl iminium ion Stereoselective reduction Cyclization Pyrrolidine |
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