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

Yu Sato
a   Division of Material Chemistry, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa, Ishikawa 920-1192, Japan
,
Takahiro Ukei
b   School of Chemistry, College of Science and Engineering, Kanazawa University, Kakuma, Kanazawa, Ishikawa 920-1192, Japan
,
Hiromasa Tsugeno
a   Division of Material Chemistry, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa, Ishikawa 920-1192, Japan
,
Takuya Suga
a   Division of Material Chemistry, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa, Ishikawa 920-1192, Japan
,
Takahiro Soeta
a   Division of Material Chemistry, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa, Ishikawa 920-1192, Japan
,
Yutaka Ukaji
a   Division of Material Chemistry, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa, Ishikawa 920-1192, Japan
› Author Affiliations
This research was partly supported by a Grant-in-Aid for Scientific Research (C) (21K05050) and (C) (18K05102) from the Ministry of Education­, Culture, Sports, Science and Technology (MEXT), Japan.


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.

Supporting Information



Publication History

Received: 28 April 2023

Accepted after revision: 17 July 2023

Accepted Manuscript online:
17 July 2023

Article published online:
25 September 2023

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