RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
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
Publikationsverlauf
Eingereicht: 28. April 2023
Angenommen nach Revision: 17. Juli 2023
Accepted Manuscript online:
17. Juli 2023
Artikel online veröffentlicht:
25. September 2023
© 2023. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1a Yamamoto H, Kawasaki M. Bull. Chem. Soc. Jpn. 2007; 80: 595
- 1b Ukaji Y. In Comprehensive Chirality, Vol. 5. Yamamoto H, Carreira E. Elsevier; Oxford: 2012: 470
- 1c Eschenbrenner-Lux V, Kumar K, Waldmann H. Angew. Chem. Int. Ed. 2014; 53: 11146
- 1d Tšupova S, Mäeorg U. Heterocycles 2014; 88: 129
- 1e Heravi MM, Ahmadi T, Ghavidel M, Heidari B, Hamidi H. RSC Adv. 2015; 5: 101999
- 2a Oelke AJ, France DJ, Hofmann T, Wuitschik G, Ley SV. Nat. Prod. Rep. 2011; 28: 1445
- 2b Dardić D, Lauro G, Bifulco G, Laboudie P, Sakhaii P, Bauer A, Vilcinskas A, Hammann PE, Plaza A. J. Org. Chem. 2017; 82: 6032
- 2c Wei Z.-W, Niikura H, Morgan KD, Vacariu CM, Andersen RJ, Ryan KS. J. Am. Chem. Soc. 2022; 144: 13556 ; and references cited therein
- 3a Arakawa Y, Goto T, Kawase K, Yoshifuji S. Chem. Pharm. Bull. 1995; 43: 535
- 3b Sakurai M, Kihara N, Watanabe N, Ikari Y, Takata T. Chem. Lett. 2018; 47: 144
- 4a Kawasaki M, Yamamoto H. J. Am. Chem. Soc. 2006; 128: 16482
- 4b Liu B, Li K.-N, Luo S.-W, Huang J.-Z, Pang H, Gong L.-Z. J. Am. Chem. Soc. 2013; 135: 3323
- 4c Liu B, Liu T.-Y, Luo S.-W, Gong L.-Z. Org. Lett. 2014; 16: 6164
- 4d Duarte VC. M, Alves MJ, Fortes AG. Synlett 2014; 25: 1751
- 4e Momiyama N, Tabuse H, Noda H, Yamanaka M, Fujinami T, Yamanishi K, Izumiseki A, Funayama K, Egawa F, Okada S, Adachi H, Terada M. J. Am. Chem. Soc. 2016; 138: 11353
- 4f Axundova FN, Kurbanova MM, Huseynzada AE, Alves MJ. Russ. J. Org. Chem. 2019; 55: 1975
- 5a Bruycker KD, Billiet S, Houck HA, Chattopadhyay S, Winne JM, Prez FE. D. Chem. Rev. 2016; 116: 3919
- 5b Siddiqi ZR, Ungarean CN, Bingham TW, Sarlah D. Org. Process Res. Dev. 2020; 24: 2953
- 6a Zhang A, Kan Y, Jiang B. Tetrahedron 2001; 57: 2305
- 6b Adam W, Bosio SG, Degen H.-G, Krebs O, Stalke D, Schumacher D. Eur. J. Org. Chem. 2002; 3944
- 6c Makino K, Henmi Y, Terasawa M, Hara O, Hamada Y. Tetrahedron Lett. 2005; 46: 555
- 6d Sasaki M, Kondo Y, Motoishi T, Kawahata M, Yamaguchi K, Takeda K. Org. Lett. 2015; 17: 1280
- 6e Tillin C, Bigler R, Calo-Lapido R, Collins BS. L, Noble A, Aggarwal VK. Synlett 2019; 30: 449
- 6f Lo VK.-Y, Chan Y.-M, Zhou D, Toy PH, Che C.-M. Org. Lett. 2019; 21: 7717
- 7a Xia D, Ukaji Y, Fujinami S, Inomata K. Chem. Lett. 2003; 32: 582
- 7b Sakai H, Xia D, Yoshida T, Fujinami S, Ukaji Y, Inomata K. Heterocycles 2008; 76: 1285
- 8 Ukaji Y, Inomata K. Chem. Rec. 2010; 10: 173
- 9 The two oxygen atoms of (ferrocenyl)acrylate were reported to coordinate zinc(II) by κ2 mode: Wang X, Liu Y, Hou H, Wu J, Fan Y. J. Organomet. Chem. 2009; 694: 77
- 10 Goodreid JD, Wong K, Leung E, McCaw SE, Gray-Owen SD, Lough A, Houry WA, Batey RA. J. Nat. Prod. 2014; 77: 2170
- 11 Bennacer B, Trubuil D, Rivalle C, Grierson DS. Eur. J. Org. Chem. 2003; 4561
- 12 Bencze LC, Filip A, Bánóczi G, Toşa MI, Irimie FD, Gellért Á, Poppe L, Paizs C. Org. Biomol. Chem. 2017; 15: 3717
- 13 Wimmer L, Schönbauer D, Pakfeifer P, Schöffmann A, Khom S, Hering S, Mihovilovic MD. Org. Biomol. Chem. 2015; 13: 990
- 14 DeBoef B, Counts WR, Gilbertson SR. J. Org. Chem. 2007; 72: 799
- 15 Iqbal Z, Han L.-C, Soares-Sello AM, Nofiani R, Thormann G, Zeeck A, Cox RJ, Willis CL, Simpson TJ. Org. Biomol. Chem. 2018; 16: 5524
- 16 Gradén H, Hallberg J, Kann N. J. Comb. Chem. 2004; 6: 783
- 17 Kawai K, Ikeda K, Sato A, Kabasawa A, Kojima M, Kokado K, Kakugo A, Sada K, Yoshino T, Matsunaga S. J. Am. Chem. Soc. 2022; 144: 1370
Representative reviews of HDA reactions:
Examples of reductive N–N bond cleavage of dehydropiperazines: