Silver-Assisted [3 + 2] Annulation of Nitrones with Isocyanides: Synthesis of 2,3,4-Trisubstituted 1,2,4-Oxadiazolidin-5-ones | Zendy

Xuanyu Shen | Zendy; Andrey Shatskiy | Zendy; Yan Chen | Zendy; Markus D. Kärkäs | Zendy; XiangShan Wang | Zendy; JianQuan Liu | Zendy

Open Access

Silver-Assisted [3 + 2] Annulation of Nitrones with Isocyanides: Synthesis of 2,3,4-Trisubstituted 1,2,4-Oxadiazolidin-5-ones

Author(s) -

Xuanyu Shen,

Andrey Shatskiy,

Yan Chen,

Markus D. Kärkäs,

XiangShan Wang,

JianQuan Liu

Publication year - 2020

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.9b03279

Subject(s) - annulation , chemistry , diastereomer , combinatorial chemistry , nucleophilic addition , molecular oxygen , catalysis , nucleophile , stereochemistry , organic chemistry

A silver-assisted method for [3 + 2] annulation of nitrones with isocyanides has been developed. The developed protocol allows access to a variety of 2,3,4-trisubstituted 1,2,4-oxadiazolidin-5-one derivatives as single diastereomers in good to excellent yields using silver oxide as the catalyst and molecular oxygen as the terminal oxidant. A plausible mechanism involving a nucleophilic addition/cyclization/protodeargentation/oxidation pathway is proposed on the basis of experimental results.

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