Regioselective Synthesis of 3-Trifluoromethylpyrroles by [3 + 2] Cycloaddition of N-Acyl α-Amino Acids and 2-Bromo-3,3,3-trifluoropropene

Weidi Zeng; Hui Li; Duozhi Wang; Lei Zhou

doi:10.1021/acs.joc.3c01611

Regioselective Synthesis of 3-Trifluoromethylpyrroles by [3 + 2] Cycloaddition of N-Acyl α-Amino Acids and 2-Bromo-3,3,3-trifluoropropene

J Org Chem. 2023 Oct 6;88(19):14088-14095. doi: 10.1021/acs.joc.3c01611. Epub 2023 Sep 12.

Authors

Weidi Zeng¹, Hui Li¹, Duozhi Wang¹, Lei Zhou^{1

2}

Affiliations

¹ State Key Laboratory of Chemistry and Utilization of Carbon Based Energy Resources, College of Chemistry, Xinjiang University, Urumqi 830046 Xinjiang, P. R. China.
² Institute of Green Chemistry and Molecular Engineering, School of Chemistry, Sun Yat-Sen University, Guangzhou 510275, China.

PMID: 37698091
DOI: 10.1021/acs.joc.3c01611

Abstract

A mild and concise method for the synthesis of 3-trifluoromethylpyrroles via base-mediated [3 + 2] cycloaddition of N-acyl α-amino acids and 2-bromo-3,3,3-trifluoropropene is described. N-Acyl α-amino acids serve as 1,3-dipole precursors without additional activating agents directly. A high level of regioselectivity was observed, regardless of the electronic nature and size of the substituents on 1,3-dipoles.