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Synthesis of 2,3-dihydropyrroles by photo rearrangement of Hantzsch 1,4-dihydropyridines with high diastereoselectivity

Author:
Zhong, Qidi, Fan, Qiangwen, Yan, Hong
Source:
Tetrahedron letters 2017
ISSN:
0040-4039
Subject:
air, aldehydes, ammonium acetate, chemical structure, irradiation, oxidation
Abstract:
The Hantzsch 1,4-dihydropyridines were found to be transforming to the 2,3-dihydropyrroles by photo rearrangement with air under irradiation of LED light (410nm) with high diastereoselectivity (dr>20:1). This reaction includes tandem photo oxidation/rearrangement. The 2,3-dihydropyrroles were obtained in moderate yields with successfully one-pot process starting from aldehydes, ammonium acetate and ethyl acetoacetate.
Agid:
5637391