Asymmetric Hetero-Diels–Alder Reaction of 4-Phenyl-1,2,4-triazole-3,5-dione with 2,4-Dienyl Carboxylic Acids

Yu Sato; Takahiro Ukei; Hiromasa Tsugeno; Takuya Suga; Takahiro Soeta; Yutaka Ukaji

doi:10.1055/a-2131-0116

Synthesis, Table of Contents

Synthesis 2023; 55(20): 3342-3348
DOI: 10.1055/a-2131-0116

paper

Asymmetric Hetero-Diels–Alder Reaction of 4-Phenyl-1,2,4-triazole-3,5-dione with 2,4-Dienyl Carboxylic Acids

Authors

Yu Sato

^aDivision of Material Chemistry, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa, Ishikawa 920-1192, Japan
Takahiro Ukei

^bSchool of Chemistry, College of Science and Engineering, Kanazawa University, Kakuma, Kanazawa, Ishikawa 920-1192, Japan
Hiromasa Tsugeno

^aDivision of Material Chemistry, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa, Ishikawa 920-1192, Japan
Takuya Suga

^aDivision of Material Chemistry, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa, Ishikawa 920-1192, Japan
Takahiro Soeta

^aDivision of Material Chemistry, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa, Ishikawa 920-1192, Japan
Yutaka Ukaji∗

^aDivision of Material Chemistry, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa, Ishikawa 920-1192, Japan

Abstract

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Abstract

The enantioselective hetero-Diels–Alder reaction of the cyclic azo compound 4-phenyl-1,2,4-triazole-3,5-dione with 2,4-dienyl carboxylic acids was performed using tartaric acid ester as the chiral auxiliary. The corresponding cycloadducts were obtained with enantioselectivities of up to 76% ee. The cis-carboxylic acid produced could be converted into the corresponding cis- and trans-methyl esters by varying the reaction conditions.

Key words

hetero-Diels–Alder reaction - 4-phenyl-1,2,4-triazole-3,5-dione - 2,4-dienyl carboxylic acid - tartaric acid ester - dehydropiperazine - methyl esterification

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References

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Supplementary Material

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