Asymmetric synthesis of 1H-pyrrol-3(2H)-ones from 2,3-diketoesters by combination of aldol condensation with benzilic acid rearrangement

Qiang Sha; Hadi Arman; Michael P Doyle

doi:10.1039/c5cc07780j

Asymmetric synthesis of 1H-pyrrol-3(2H)-ones from 2,3-diketoesters by combination of aldol condensation with benzilic acid rearrangement

Chem Commun (Camb). 2016 Jan 4;52(1):108-11. doi: 10.1039/c5cc07780j.

Authors

Qiang Sha¹, Hadi Arman², Michael P Doyle²

Affiliations

¹ School of Chemical Engineering, Nanjing University of Science and Technology, Xiao Ling Wei 200, Nanjing 210094, P. R. China and Department of Chemistry, The University of Texas at San Antonio, San Antonio, Texas 78249, USA. michael.doyle@utsa.edu.
² Department of Chemistry, The University of Texas at San Antonio, San Antonio, Texas 78249, USA. michael.doyle@utsa.edu.

Abstract

An efficient two-step protocol for the asymmetric synthesis of 1H-pyrrol-3(2H)-one derivatives in 99% ee from conveniently accessed 2,3-diketoesters has been developed.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Aldehydes / chemical synthesis
Aldehydes / chemistry*
Benzilates / chemistry*
Esterification
Ketones / chemical synthesis
Ketones / chemistry
Models, Molecular
Pyrroles / chemical synthesis*
Pyrroles / chemistry

Substances

Aldehydes
Benzilates
Ketones
Pyrroles
3-hydroxybutanal

Abstract

Publication types

MeSH terms

Substances

Grants and funding