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* and Lei Zhou*
*Xinjiang University, Urumqi 830046 Xinjiang; Sun Yat-Sen
University, Guangzhou 510275, China, Email: xjwangdz
sina.com,
zhoul39mail.sysu.edu.cn
W. Zeng, H. Li, D. Wang, L. Zhou, J. Org. Chem., 2023, 88, 14088-14095.
DOI: 10.1021/acs.joc.3c01611
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Abstract
A base-mediated [3 + 2] cycloaddition of N-acyl α-amino acids to 2-bromo-3,3,3-trifluoropropene (BTP) provides 3-trifluoromethylpyrroles. 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.
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proposed reaction pathway
Key Words
ID: J42-Y2023
