Issue 66, 2022

Deconstructive isomerization of azetidinols via C–C bond cleavage enabled by N-heterocyclic carbene (NHC) catalysis

Abstract

Herein, we describe an N-heterocyclic carbene (NHC)-catalyzed deconstructive isomerization of azetidinols via an inert C–C bond cleavage. It provides a direct and supplementary pathway to access α-amino ketone and oxazol-2-one derivatives in moderate to good yields. DFT calculation supports the proposed mechanism in which NHC undergoes a concerted proton transfer and ring-opening process. This reaction features non-metal catalysis, simple reaction operation, excellent regioselectivity and gram-scale synthesis.

Graphical abstract: Deconstructive isomerization of azetidinols via C–C bond cleavage enabled by N-heterocyclic carbene (NHC) catalysis

Supplementary files

Article information

Article type
Communication
Submitted
01 Jun 2022
Accepted
22 Jul 2022
First published
25 Jul 2022

Chem. Commun., 2022,58, 9294-9297

Deconstructive isomerization of azetidinols via C–C bond cleavage enabled by N-heterocyclic carbene (NHC) catalysis

Z. Wang, X. Chen, Y. Hu, H. Li, Y. Yang, Y. Liu, H. Jin and B. Zhou, Chem. Commun., 2022, 58, 9294 DOI: 10.1039/D2CC03104C

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