1, 2??Asymmetric Induction in Diastereoselective Zwitterionic Aza??Claisen Rearrangements: Key Steps in Optically Active Alkaloid Synthesis

…, D Schollmeyer, U Nubbemeyer

Index: Heescher, Carolin; Schollmeyer, Dieter; Nubbemeyer, Udo European Journal of Organic Chemistry, 2013 , # 20 p. 4399 - 4404

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Abstract

Abstract The zwitterionic aza-Claisen rearrangement of optically active N-allylpyrrolidines and α-phenoxyacetyl fluorides proceeds with complete simple diastereoselectivity (internal asymmetric induction) and complete 1, 2-asymmetric induction to generate a new C–C bond adjacent to a chiral CN-Boc functionality. The resulting γ, δ-unsaturated amides were cyclised to give the corresponding pyrrolizidinones, which enabled the determination of ...

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