Cycloadditions between methyl (Z)-2-bromo-4,4,4-trifluoro-2-butenoate and various tosylacetamides: Synthesis of trifluoromethylated pyroglutamates and 2-pyridones derivatives

Hong Hai Zhang; Wei Shen; Long Lu

doi:10.1016/j.tetlet.2018.01.095

Cycloadditions between methyl (Z)-2-bromo-4,4,4-trifluoro-2-butenoate and various tosylacetamides: Synthesis of trifluoromethylated pyroglutamates and 2-pyridones derivatives

Hong Hai Zhang, Wei Shen, Long Lu

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

5 Scopus citations

Abstract

Cycloaddition reactions between methyl (Z)-2-bromo-4,4,4-trifluoro-2-butenoate and various 2-tosylacetamides are described. Various 2-tosylacetamides react with methyl (Z)-2-bromo-4,4,4-trifluoro-2-butenoate in the presence of NaH at room temperature in one step to form trifluoromethylated pyroglutamates as single diastereomers. However, employing the same reactants using t-BuOK as base at −78 °C results in the formation of trifluoromethylated 2-pyridones. A ring-closure mechanism is proposed for the reaction.

Original language	English
Pages (from-to)	1042-1045
Number of pages	4
Journal	Tetrahedron Letters
Volume	59
Issue number	11
DOIs	https://doi.org/10.1016/j.tetlet.2018.01.095
State	Published - Mar 14 2018
Externally published	Yes

Funding

We thank the National Natural Science Foundation of China (Grant Numbers 21704041 and 29825104 ) and the Chinese Academy of Science for the financial support. A We thank the National Natural Science Foundation of China (Grant Numbers 21704041 and 29825104) and the Chinese Academy of Science for the financial support.

Keywords

Cycloaddition
Fluorinated building block
Trifluoromethylated dihydropyridine
Trifluoromethylated proglutamate

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10.1016/j.tetlet.2018.01.095

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title = "Cycloadditions between methyl (Z)-2-bromo-4,4,4-trifluoro-2-butenoate and various tosylacetamides: Synthesis of trifluoromethylated pyroglutamates and 2-pyridones derivatives",

abstract = "Cycloaddition reactions between methyl (Z)-2-bromo-4,4,4-trifluoro-2-butenoate and various 2-tosylacetamides are described. Various 2-tosylacetamides react with methyl (Z)-2-bromo-4,4,4-trifluoro-2-butenoate in the presence of NaH at room temperature in one step to form trifluoromethylated pyroglutamates as single diastereomers. However, employing the same reactants using t-BuOK as base at −78 °C results in the formation of trifluoromethylated 2-pyridones. A ring-closure mechanism is proposed for the reaction.",

keywords = "Cycloaddition, Fluorinated building block, Trifluoromethylated dihydropyridine, Trifluoromethylated proglutamate",

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T1 - Cycloadditions between methyl (Z)-2-bromo-4,4,4-trifluoro-2-butenoate and various tosylacetamides

T2 - Synthesis of trifluoromethylated pyroglutamates and 2-pyridones derivatives

AU - Zhang, Hong Hai

AU - Shen, Wei

AU - Lu, Long

PY - 2018/3/14

Y1 - 2018/3/14

N2 - Cycloaddition reactions between methyl (Z)-2-bromo-4,4,4-trifluoro-2-butenoate and various 2-tosylacetamides are described. Various 2-tosylacetamides react with methyl (Z)-2-bromo-4,4,4-trifluoro-2-butenoate in the presence of NaH at room temperature in one step to form trifluoromethylated pyroglutamates as single diastereomers. However, employing the same reactants using t-BuOK as base at −78 °C results in the formation of trifluoromethylated 2-pyridones. A ring-closure mechanism is proposed for the reaction.

AB - Cycloaddition reactions between methyl (Z)-2-bromo-4,4,4-trifluoro-2-butenoate and various 2-tosylacetamides are described. Various 2-tosylacetamides react with methyl (Z)-2-bromo-4,4,4-trifluoro-2-butenoate in the presence of NaH at room temperature in one step to form trifluoromethylated pyroglutamates as single diastereomers. However, employing the same reactants using t-BuOK as base at −78 °C results in the formation of trifluoromethylated 2-pyridones. A ring-closure mechanism is proposed for the reaction.

KW - Cycloaddition

KW - Fluorinated building block

KW - Trifluoromethylated dihydropyridine

KW - Trifluoromethylated proglutamate

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Cycloadditions between methyl (Z)-2-bromo-4,4,4-trifluoro-2-butenoate and various tosylacetamides: Synthesis of trifluoromethylated pyroglutamates and 2-pyridones derivatives

Abstract

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Keywords

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