Asymmetric Neber Reaction in the Synthesis of Chiral 2-(Tetrazol-5-yl)-2H-Azirines,Synlett

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Asymmetric Neber Reaction in the Synthesis of Chiral 2-(Tetrazol-5-yl)-2H-Azirines
Synlett ( IF 1.7 ) Pub Date : 2019-12-17 , DOI: 10.1055/s-0039-1691533
Cláudia Alves ₁ , Carla Grosso ₁ , Pedro Barrulas _{2,

3} , José A. Paixão ₄ , Ana L. Cardoso ₁ , Anthony J. Burke ₂ , Américo Lemos _{1,

5} , Teresa M. V. D. Pinho e Melo ₁

Affiliation

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.

中文翻译：

手性 2-(Tetraazol-5-yl)-2H-Azirines 合成中的不对称 Neber 反应

已经建立了一种成功的一锅法合成手性 2-四唑基-2H-氮丙啶，采用有机催化。该协议涉及 β-酮肟-1H-四唑的原位甲苯磺酰化，然后在手性有机催化剂的存在下进行 Neber 反应。在有机催化剂中，研究了一种衍生自 6β-氨基青霉烯酸的新型硫脲催化剂，该催化剂具有出色的对映选择性。

更新日期：2019-12-17

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