Asymmetric neber reaction in the Synthesis of Chiral 2-(Tetrazol-5-yl)-2H-Azirines

Alves, Claudia; Grosso, Carla; Barrulas, Pedro; Paixao, Jose A.; Cardoso, Ana L.; Burke, Anthony J.; Lemos, Americo; Pinho e Melo, Teresa M. V. D.

http://hdl.handle.net/10400.1/16529

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Authors

Pinho e Melo, Teresa M. V. D.

Abstract(s)

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 beta-ketoxime-1H-tetrazoles followed by the Neber reaction, in the presence of chiral organocatalysts. Among the organocatalysts studied a novel thiourea catalyst derived from 6 beta-aminopenicillanic acid afforded excellent enantioselectivities.