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Stereoselective assembly of 3,4-epoxypyrrolines via nucleophilic addition induced domino cyclization of 6-halo-1-oxa-4-azahexatrienes

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Abstract

A two-step method for the preparation of 3,4-epoxypyrroline derivatives (6-oxa-3-azabicyclo[3.1.0]hex-2-enes) from 2-halo-2H-azirine-2-carboxylates, diazo keto esters, and amines has been developed. 6-Halo-1-oxa-4-azahexa-1,3,5-trienes, prepared in the first step from the azirines and diazo compounds under Rh(II) catalysis, were subjected to nucleophile-induced tandem cyclization to afford highly functionalized rac-(1R,4R,5S)-6-oxa-3-azabicyclo[3.1.0]hex-2-enes in good yields. The stereochemical outcome of the tandem cyclization induced by the secondary amines is rationalized in terms of the structural rigidity of the betaine-type precursor due to the hydrogen bonding between the ammonium group and ester group adjacent to the halogen atom. Post-modification of the 3,4-epoxypyrrolines by the Stille cross-coupling, reduction, and UV-irradiation was also demonstrated.

Graphical abstract: Stereoselective assembly of 3,4-epoxypyrrolines via nucleophilic addition induced domino cyclization of 6-halo-1-oxa-4-azahexatrienes

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Article information


Submitted
23 Nov 2019
Accepted
25 Dec 2019
First published
26 Dec 2019

Org. Chem. Front., 2020, Advance Article
Article type
Research Article

Stereoselective assembly of 3,4-epoxypyrrolines via nucleophilic addition induced domino cyclization of 6-halo-1-oxa-4-azahexatrienes

I. A. Smetanin, A. V. Agafonova, N. V. Rostovskii, A. F. Khlebnikov, D. S. Yufit and M. S. Novikov, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/C9QO01401B

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