Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Download PDF
Synthesis 2020; 52(20): 2987-3000
DOI: 10.1055/s-0040-1707897
DOI: 10.1055/s-0040-1707897
paper
Tetrasubstituted Furans by Nucleophile-Induced Cleavage of Carbonyl Ylide–DMAD Cycloadducts
Further Information
Publication History
Received: 06 May 2020
Accepted after revision: 27 May 2020
Publication Date:
20 July 2020 (online)
Abstract
Compounds incorporating a 4-aza-8-oxabicyclo[3.2.1]oct-6-en-2-one moiety, which were prepared by a tandem carbenoid carbonyl ylide cyclization/[3+2]-cycloaddition reaction from ethyl 2-diazo-3-oxo-4-phthalimidobutanoates, undergo a nucleophile-induced two-bond ring cleavage when treated with protic heteronucleophiles. In this manner, tetrasubstituted furantricarboxylates, tethered with α-amino acids, esters, thioesters, and amides by a 2-carbonylphenyl moiety, are obtained.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707897.
- Supporting Information
-
References
- 1 Review: McMills MC, Wright D. Carbonyl Ylides . In Chemistry of Heterocyclic Compounds, Vol. 59. Padwa A, Pearson WH. John Wiley & Sons; Hoboken: 2003: 253-314
- 2 Review: Hodgson DM, Labande AH, Muthusamy S. Org. React. (N. Y.) 2013; 80: 133
- 3 Review: Suga H, Itoh K. Recent Advances in Catalytic Asymmetric 1,3-Dipolar Cycloadditions of Azomethine Imines, Nitrile Oxides, Diazoalkanes, and Carbonyl Ylides. In Methods and Applications of Cycloaddition Reactions in Organic Syntheses. Nishiwaki N. John Wiley & Sons; Hoboken: 2014: 175-204
- 5 Review: France S, Phun LH. Curr. Org. Synth. 2010; 7: 332
- 6 Minireview: Padwa A. Russ. Chem. Bull. 2016; 65: 2183
- 7 Doyle MP, McKervey MA, Ye T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: from Cyclopropanes to Ylides. Wiley; New York: 1995
- 8a Li Y, Zhang Q, Zhai H. Org. Lett. 2016; 18: 4076
- 8b Yuan H, Gong J, Yang Z. Org. Lett. 2016; 18: 5500
- 8c Kahar N, Jadhav P, Reddy RV. R, Dawande S. Chem. Commun. 2020; 56: 1207
- 9 For a review see: Padwa A. Acc. Chem. Res. 1991; 24: 22
- 10a Padwa A, Hertzog DL, Chinn RL. Tetrahedron Lett. 1989; 30: 4077
- 10b Padwa A, Dean DC, Hertzog DL, Nadler WR, Zhi L. Tetrahedron 1992; 48: 7565
- 11a Nikolaev V, Krylov IS, Schulze B, Rodina L. Russ. J. Org. Chem. 2005; 41: 784
- 11b Nikolaev V, Hennig L, Sieler J, Rodina L, Schulze B, Nikolaev V. Org. Biomol. Chem. 2005; 3: 4108
- 12 Navickas V, Ushakov DB, Maier ME, Ströbele M, Meyer J.-J. Org. Lett. 2010; 12: 3418
- 13a Hodgson DM, Glen R, Grant GH, Redgrave AJ. J. Org. Chem. 2003; 68: 581
- 13b Shimada N, Hanari T, Kurosaki Y, Takeda K, Anada M, Nambu H, Shiro M, Hashimoto S. J. Org. Chem. 2010; 75: 6039
- 14a Enßle M, Buck S, Werz R, Maas G. ARKIVOC 2012; (iii): 149
- 14b Enßle M, Buck S, Werz R, Maas G. Beilstein J. Org. Chem. 2012; 8: 433
- 15 Nakhla MC, Lee C.-W, Wood JL. Org. Lett. 2015; 17: 5760
- 16 Padwa A, Zhi L, Fryxell GE. J. Org. Chem. 1991; 56: 1077
- 17a König B. In Science of Synthesis, Vol. 9. Maas G. Thieme; Stuttgart: 2000: 183-285
- 17b Keay BA. Chem. Soc. Rev. 1999; 28: 209
- 18a Gulevich AV, Dudnik AS, Chernyak N, Gevorgyan V. Chem. Rev. 2013; 113: 3084
- 18b Moran WJ, Rodgriuez A. Org. Prep. Proced. Int. 2012; 44: 103
- 18c Kirsch SF. Org. Biomol. Chem. 2006; 4: 2076
- 18d Brown RC. D. Angew. Chem. Int. Ed. 2005; 44: 850
- 19a Liu W, Jiang H, Zhang M, Qi C. J. Org. Chem. 2010; 75: 966
- 19b Yang Y, Jao J, Zhang Y. Org. Lett. 2013; 15: 3206
- 19c Palisse A, Kirsch SF. Eur. J. Org. Chem. 2014; 7095
- 19d Schmidt D, Malkar CC, Beifuss U. Org. Lett. 2014; 16: 4862
- 19e Wu J, Yoshikai N. Angew. Chem. Int. Ed. 2015; 54: 11107
- 19f Manna S, Antonchick AP. Org. Lett. 2015; 17: 4300
- 20 Deepthi A, Babu BP, Balachandran B. Org. Prep. Proced. Int. 2019; 51: 409
- 21a Fan M, Yan Z, Liu W, Liang Y. J. Org. Chem. 2005; 70: 8204
- 21b Yavari I, Mokhtarporyani-Sanandaj A, Moradi L, Mirzaei A. Tetrahedron 2008; 64: 5221
- 21c Kao T.-T, Syu S.-E, Jhang Y.-W, Lin W. Org. Lett. 2010; 12: 3066
- 21d Dong J, Du H, Xu J. RSC Adv. 2019; 9: 25034
- 21e Nazeri MT, Mohammadian R, Farhid H, Shaabani A, Notash B. Tetrahedron Lett. 2020; 61: 151408
- 22 Guthrie JP. Can. J. Chem. 1974; 52: 2037
- 23a Neh H, Blechert S, Schnick W, Jansen M. Angew. Chem. Int. Ed. 1984; 23: 905
- 23b Kaneko C, Katagiri N, Sato M, Muto M, Sakamoto T, Saikawa S, Naito T, Saito A. J. Chem. Soc., Perkin Trans. 1 1986; 1283
- 23c Katagiri N, Tomura M, Haneda T, Kaneko C. J. Chem. Soc., Chem. Commun. 1987; 1422
- 23d Wilson KE, Tsou NN, Guan Z, Ruby CL, Pelaez F, Gorrochategui J, Vicente F, Onishi HR. Tetrahedron Lett. 2000; 41: 8705
- 24 Rainier JD, Xu Q. Org. Lett. 1999; 1: 27
- 25a Antos JM, Francis MB. J. Am. Chem. Soc. 2004; 126: 102566
- 25b Antos JM, McFarland JM, Iavarone AT, Francis MB. J. Am. Chem. Soc. 2009; 131: 6301
- 26 Himaja M, Harish KumarK, Ramana MV, Belagali LS. Eur. J. Med. Chem. 1999; 34: 525
- 27 Zhang J, Li X, Jiang Y, Feng J, Li X, Zhang Y, Xu WJ. Bioorg. Med. Chem. 2014; 22: 3055
- 28a SHELXS97: Sheldrick GM. Acta Crystallogr., Sect A 2008; 64: 112
- 28b SHELXL-2014: Sheldrick GM. Acta Crystallogr., Sect. C 2015; 71: 3
- 29 ORTEP-3 for Windows: Farrugia LJ. J. Appl. Crystallogr. 2012; 45: 849
Selected recent examples:
Selected examples:
Selected examples: