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Asymmetric Neber Reaction in the Synthesis of Chiral 2-(Tetrazol-5-yl)-2H- Azirines
Authors: Cláudia C. Alves; Carla Grosso; Pedro Barrulas; José A. Paixão; Ana L. Cardoso; Anthony J. Burke; Américo Lemos; Teresa M. V. D. Pinho e Melo
Ref.: Synlett 31(6), 553-558 (2020)
Abstract: A successful one-pot methodology for the synthesis of chiral 2-tetrazolyl-2H-azirines has been established, resorting to organocatalysis. The protocol involves the in situ tosylation of β-ketoxime-1H-tetrazoles followed by the Neber reaction, in the presence of chiral organocatalysts. Among the organocatalysts studied a novel thiourea catalyst derived from 6β-aminopenicillanic acid afforded excellent enantioselectivities.
