Synthesis and reactivity of enantiomerically pure N-alkyl-2-alkenyl azetidinium salts |
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Authors: | Franç ois Couty,Franç ois Durrat,Gwilherm Evano,Damien Prim |
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Affiliation: | SIRCOB, UMR CNRS 8086, Université de Versailles, 45, avenue des Etats-Unis, 78035, Versailles Cédex, France |
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Abstract: | A synthesis of stereodefined enantiomerically pure 2-alkenyl azetidines is described using Wittig olefination as key step. The quaternary triflate ammonium salts of these heterocycles were prepared in a stereoselective way and treatment of these azetidinium salts with a base (KHMDS or PhLi) induced a regioselective Stevens rearrangement leading to a 3-alkenyl pyrrolidine. An unprecedented SN2′ reaction involving phenyllithium as nucleophile and an ammonium as leaving group was observed in one case. |
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Keywords: | Azetidines Ring expansions |
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