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

A mild and concise method for the synthesis of 3-trifluoromethylpyrroles via base-mediated [3 + 2] cycloaddition of N-acyl a-amino acids and 2-bromo-3,3,3-trifluoropropene is described. N-Acyl a-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.

Automated summary

A mild and convenient method for the synthesis of 3-trifluoromethylpyrroles via base-mediated [3 + 2] cycloaddition has been described. N-Acyl a-amino acids serve as 1,3-dipole precursors without the need for additional activating agents. The reaction exhibits a high level of regioselectivity, regardless of the electronic nature and size of the substituents on the 1,3-dipoles.