Asymmetric 1,4-Addition of Diarylphosphine Oxides to α,β-Unsaturated 2-Acyl Imidazoles

Lirong Chen; Guiyong Wang; Xiufei Nong; Wendi Shao; Jiuling Li; Yafei Guo; Baomin Fan

doi:10.1002/chem.202401017

Asymmetric 1,4-Addition of Diarylphosphine Oxides to α,β-Unsaturated 2-Acyl Imidazoles

Chemistry. 2024 Apr 23:e202401017. doi: 10.1002/chem.202401017. Online ahead of print.

Authors

Lirong Chen¹, Guiyong Wang¹, Xiufei Nong¹, Wendi Shao¹, Jiuling Li¹, Yafei Guo², Baomin Fan¹

Affiliations

¹ Yunnan Minzu University, School of Chemistry & Environment, CHINA.
² YNAU: Yunnan Minzu University, School of chemistry and environment, Yuehua street, 650500, kunming, CHINA.

PMID: 38652470
DOI: 10.1002/chem.202401017

Abstract

Here we introduce a metal-free, catalytic and enantioselective strategy from α,β-unsaturated 2-acyl imidazoles to the chiral phosphorous 2-acyl imidazoles. Interestingly, this methodology was catalyzed by the classical and commercial oxazaborolidine under mild conditions. This strategy features a wide range of substrates scope with good yields and excellent enantioselectivities. The possible mechanism further suggests the key of this reaction through the cleavage of diarylphosphine oxides using Frustrated Lewis Pairs theory.

Keywords: asymmetric 1,4-addition; diarylphosphine oxides; metal-free; oxazaborolidine; α,β-unsaturated 2-acyl imidazoles.