Reaction of alpha-(N-carbamoyl)alkylcuprates with enantioenriched propargyl electrophiles: synthesis of enantioenriched 3-pyrrolines |
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Authors: | Dieter R Karl Chen Ningyi Gore Vinayak K |
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Affiliation: | Howard L. Hunter Chemistry Laboratory, Clemson University, Clemson, South Carolina 29634-0973, USA. dieterr@clemson.edu |
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Abstract: | Enantioenriched propargyl mesylates or perfluorobenzoates react with alpha-(N-carbamoyl)alkylcuprates to afford scalemic alpha-(N-carbamoyl) allenes which undergo N-Boc deprotection and AgNO3-promoted cyclization to afford N-alkyl-3-pyrrolines. The synthetic sequence proceeds under optimal conditions with no loss of enantiopurity relative to the starting propargyl alcohols prepared by asymmetric addition of terminal alkynes to aldehydes. |
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