Stereoselective Biginelli-like reaction catalyzed by a chiral phosphoric acid bearing two hydroxy groups

Xiaoyun Hu; Jianxin Guo; Cui Wang; Rui Zhang; Victor Borovkov

doi:10.3762/bjoc.16.155

Stereoselective Biginelli-like reaction catalyzed by a chiral phosphoric acid bearing two hydroxy groups

Beilstein J Org Chem. 2020 Jul 31:16:1875-1880. doi: 10.3762/bjoc.16.155. eCollection 2020.

Authors

Xiaoyun Hu¹, Jianxin Guo¹, Cui Wang¹, Rui Zhang¹, Victor Borovkov²

Affiliations

¹ College of Chemistry and Materials South-Central University for Nationalities, Wuhan, China.
² Department of Chemistry and Biotechnology, Tallinn University of Technology, Akadeemia tee 15, Tallinn 12618, Estonia.

Abstract

To develop new efficient stereoselective catalysts for Biginelli-like reactions, a chiral phosphoric acid bearing two hydroxy groups derived from ʟ-tartaric acid was successfully synthesized via highly regioselective transformations of enantiopure 1,1,4,4-tetraphenylbutanetetraol. The obtained catalyst effectively catalyzed Biginelli-like reactions with moderate to good enantioselectivities. Control experiments indicated that the presence of the two hydroxy groups were indispensable for achieving a high enantioselectivity.

Keywords: asymmetric Biginelli-like reaction; chiral 1,1,4,4-tetraphenylbutanetetraol; chiral phosphoric acid.

Grants and funding

The National Nature Science Foundation of China (No.21302233), the Nature Science Foundation of Hubei Province of China (No. 2012FFB07410) and the Fundamental Research Funds for the Central Universities, South-Central University for Nationalities (CZY20016) are acknowledged for financial support.