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Synthesis 2023; 55(20): 3342-3348
DOI: 10.1055/a-2131-0116
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
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.
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 esterificationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2131-0116.
- 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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Representative reviews of HDA reactions:
Examples of reductive N–N bond cleavage of dehydropiperazines: