Abstract

The enantiomerically pure ( S)-5-(tosylmethyl)-2-pyrrolidinone 2, prepared from commercially available ( S)-pyroglutaminol, is dialkylated at the nitrogen atom and the α-sulfonyl position using several dielectrophiles using sodium hydride as the base to diastereoselectively afford indolizidine derivatives 5 and the less common hexahydropyrrolo[1,2- a]azepin-3-one 6 in moderate to good yield. This domino process has been applied to the synthesis of (−)-δ-coniceine.

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