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

Weidi Zeng, Hui Li, Duozhi Wang^*, Lei Zhou^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

2 Citations (Scopus)

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.

Original language	English
Pages (from-to)	14088-14095
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	88
Issue number	19
DOIs	https://doi.org/10.1021/acs.joc.3c01611
Publication status	Published - 6 Oct 2023
Externally published	Yes

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Zeng, W., Li, H., Wang, D., & Zhou, L. (2023). Regioselective Synthesis of 3-Trifluoromethylpyrroles by [3 + 2] Cycloaddition of N-Acyl α-Amino Acids and 2-Bromo-3,3,3-trifluoropropene. Journal of Organic Chemistry, 88(19), 14088-14095. https://doi.org/10.1021/acs.joc.3c01611

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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.",

author = "Weidi Zeng and Hui Li and Duozhi Wang and Lei Zhou",

note = "Publisher Copyright: {\textcopyright} 2023 American Chemical Society",

year = "2023",

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doi = "10.1021/acs.joc.3c01611",

language = "English",

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AU - Zeng, Weidi

AU - Li, Hui

AU - Wang, Duozhi

AU - Zhou, Lei

PY - 2023/10/6

Y1 - 2023/10/6

N2 - 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.

AB - 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.

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U2 - 10.1021/acs.joc.3c01611

DO - 10.1021/acs.joc.3c01611

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

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ER -

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

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