Synthesis, Inhaltsverzeichnis Synthesis 2022; 54(07): 1870-1876DOI: 10.1055/s-0041-1737817 paper Diastereoselective Synthesis of Spirocyclopentene-Indanediones from Isocyanides, Acetylenic Esters, and NH-Acidic Compounds Issa Yavari ∗ , Parisa Ravaghi , Maryam Safaei Artikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Abstract A diastereoselective synthesis of spirocyclopentene-1H-indene-1,3(2H)-diones through a three-component reaction of alkyl isocyanides, dialkyl acetylenedicarboxylates, and 2-(alkylamino)-2-(1,3-dioxo-1H-inden-2(3H)-ylidene)acetonitriles is described. This reaction forms two stereogenic centers with remarkable diastereoselectivity. The crystal structure of a typical product has been determined by X-ray diffraction. Key words Key wordsspriro compounds - diastereoselective synthesis - alkyl isocyanides - Huisgen zwitterion - ninhydrin Volltext Referenzen References 1a Tietze LF. Chem. Rev. 1996; 96: 115 1b Tietze LF, Beifuss U. Angew. Chem. Int. Ed. 1993; 32: 131 1c Pellissier H. Tetrahedron 2006; 62: 1619 1d Pellissier H. Tetrahedron 2006; 62: 2143 1e Padwa A, Bur SK. Tetrahedron 2007; 63: 5341 1f Nicolaou KC, Edmonds DJ, Bulger PG. Angew. Chem. Int. Ed. 2006; 45: 7134 1g Wasilke JC, Obrey SJ, Baker RT, Bazan GC. Chem. Rev. 2005; 105: 1001 1h Chapman C, Frost C. Synthesis 2007; 1 1i Enders D, Grondal C, Hüttl MR. M. Angew. Chem. Int. Ed. 2007; 46: 1570 2a Trost BM. Angew. Chem. Int. Ed. 1995; 34: 259 2b Sheldon RA. Pure Appl. Chem. 2000; 72: 1233 3a Nenajdenko VG. Isocyanide Chemistry. Applications in Synthesis and Material Science. Wiley-VCH; Weinheim: 2012 3b Dömling A. Chem. Rev. 2006; 106: 17 4a Oakes TR, Donovan DJ. J. Org. Chem. 1973; 38: 1319 4b Yavari I, Davar-Panah M, Heydari M, Najafian K, Zonouzi A. Monatsh. Chem. 1996; 127: 963 5 Rostamnia S. RSC Adv. 2015; 5: 97044 6a Eliel EL, Wilen SH, Mander LN. Stereochemistry of Organic Compounds. Wiley; New York: 1994: 1119 6b Ding A, Meazza M, Guo H, Yang JW, Rios R. Chem. Soc. Rev. 2018; 47: 5946 6c Rios R. Chem. Soc. Rev. 2012; 41: 1060 6d Marson CM. Chem. Soc. Rev. 2011; 40: 5514 7a Franz AK, Hanhan NV, Ball-Jones NR. ACS Catal. 2013; 3: 540 7b Müller G, Berkenbosch T, Benningshof JC. J, Stumpfe D, Bajorath J. Chem. Eur. J. 2017; 23: 703 7c Smith LK, Baxendale IR. Org. Biomol. Chem. 2015; 13: 9907 7d Zheng Y, Tice CM, Singh SB. Bioorg. Med. Chem. Lett. 2014; 24: 3673 8a Carreira EM, Fessard TC. Chem. Rev. 2014; 114: 8257 8b Bartoli A, Rodier F, Commeiras L, Parrain JL, Chouraqui G. Nat. Prod. Rep. 2011; 28: 763 8c Hong L, Wang R. Adv. Synth. Catal. 2013; 355: 1023 9a Pandey RC, Toussaint MW, Stroshane RM, Kalita CC, Aszalos AA, Garretson AL, Wei TT, Byrne KM, Geoghegan RF, White RJ. J. Antibiot. 1981; 34: 1389 9b Kotha S, Cheekatla SR, Fatma A. ACS Omega 2019; 4: 17109 9c Kotha S, Fatma A. Asian J. Org. Chem. 2021; 10: 129 10a Goto K, Sudzuki H. Bull. Chem. Soc. Jpn. 1929; 4: 220 10b Tomita M, Okamoto Y, Kikuchi T, Osaki K, Nishikawa M, Kamiya K, Sasaki Y, Matoba K, Goto K. Chem. Pharm. Bull. 1971; 19: 770 11a Ball-Jones NR, Badillo JJ, Tran NT, Franz AK. Angew. Chem. Int. Ed. 2014; 53: 9462 11b Zhou J, Wang Q.-L, Peng L, Tian F, Xu X.-Y, Wang L.-X. Chem. Commun. 2014; 14601 11c Sun Q.-S, Zhu H, Chen Y.-J, Yang X.-D, Sun X.-W, Lin G.-Q. Angew. Chem. Int. Ed. 2015; 54: 13253 11d Patra A, Bhunia A, Yetra SR, Gonnade RG, Biju AT. Org. Chem. Front. 2015; 2: 1584 11e Zhang X.-Y, Shen Z, Hua L.-L, Wang L.-J, Lin Y.-S, Xie J.-W, Cui H.-L. Tetrahedron Lett. 2016; 57: 3790 11f Gicquel M, Gomez C, Alvarez MC. C, Pamlard O, Jacquet VG. E, Bignon J, Voituriez A, Marinetti A. J. Med. Chem. 2018; 61: 9386 11g Luo W, Shao B, Li J, Song D, Yi X, Ling F, Zhong W. Tetrahedron Lett. 2019; 60: 151206 12a Yavari I, Sheikhi S, Sheykhahmadi J, Taheri Z, Halvagar MR. Synthesis 2021; 53: 2057 12b Yavari I, Solgi R, Khajeh-Khezri A, Askarian-Amiri M, Halvagar MR. J. Heterocycl. Chem. 2019; 56: 3396 12c Yavari I, Askarian-Amiri M, Taheri Z. Monatsh. Chem. 2019; 150: 1093 12d Yavari I, Khajeh-Khezri A, Aliveisi R, Halvagar MR. J. Phys. Org. Chem. 2018; 31: e3871 12e Yavari I, Naeimabadi M, Halvagar MR. Tetrahedron 2018; 74: 4145 12f Yavari I, Hojati M, Azad L, Halvagar MR. Synlett 2018; 29: 1024 12g Yavari I, Naeimabadi M, Sheykhahmadi J, Bahemmat S, Halvagar MR. ChemistrySelect 2017; 2: 11370 13 For a recent review, see: Das S. RSC Adv. 2020; 10: 18875 14 Grigg R, Mongkolaussavaratana T. J. Chem. Soc., Perkin Trans. 1 1988; 541 15 CCDC 1996238 (4b) contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures. Zusatzmaterial Zusatzmaterial Supporting Information
