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-00000083.xml
Synlett 2013; 24(15): 1937-1940
DOI: 10.1055/s-0033-1339520
DOI: 10.1055/s-0033-1339520
letter
Stereoselective Synthesis of New β-Lactams from 2-(1H-Pyrrol-1-yl)-1-propen-1-one as a Novel Ketene
Further Information
Publication History
Received: 31 May 2013
Accepted after revision: 16 July 2013
Publication Date:
14 August 2013 (online)
Abstract
New trans-β-lactams have been stereoselectively prepared by the reaction of N-pyrrolylpropanoic acid with 2-chloro-1-methylpyridinium iodide and aromatic imines in the presence of triethylamine as a base via in situ generation of methyl-2-(1H-pyrrol-1-yl)ketene as a novel heteroarylketene. The trans-β-lactam was formed either as a single isomer or as the major isomer.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
-
References
- 1 Leung-Toung R, Tidwell TT. J. Am. Chem. Soc. 1990; 112: 1042
- 2 Tsuda T, Hokazono H, Toyota K. J. Chem. Soc., Chem. Commun. 1995; 2417
- 3 Sharma AK, Mahajan MP. Tetrahedron 1997; 53: 13841
- 4 Bandyopadhyay D, Cruz J, Banik BK. Tetrahedron 2012; 68: 10686
- 5 Liu R, Tidwell TT. Can. J. Chem. 1995; 73: 1818
- 6 Allen AD, Tidwell TT. Eur. J. Org. Chem. 2012; 1081
- 7 Staudinger H. Ber. Dtsch. Chem. Ges. 1905; 38: 1735
- 8 Duckworth AC. J. Org. Chem. 1962; 27: 3146
- 9 Penn JH, Owens WH. J. Am. Chem. Soc. 1993; 115: 82
- 10 Baigrie LM, Seikaly HR, Tidwell TT. J. Am. Chem. Soc. 1985; 107: 5391
- 11 Leung-Toung R, Wentrup C. J. Org. Chem. 1992; 57: 4850
- 12 Leung-Toung R, Peterson MR, Tidwell TT, Csizmadia IG. J. Mol. Struct. 1989; 183: 319
- 13 Alonso G, Lόpez-Ortiz F, del Pozo C, Peralta E, Macίas A, González J. J. Org. Chem. 2001; 66: 6333
- 14 Bennett DM, Okamoto I, Danheiser RL. Org. Lett. 1999; 1: 641
- 15 Chen YP, Chantegrel B, Deshayes S. Heterocycles 1995; 41: 175
- 16 Matsui S, Kinbara K, Saigo K. Tetrahedron Lett. 1999; 40: 899
- 17 Brady WT, Saidi K. J. Org. Chem. 1979; 44: 733
- 18 Bittner J, Seppelt K. Chem. Ber. 1990; 123: 2187
- 19 Montaigne R, Ghosez L. Angew. Chem., Int. Ed. Engl. 1968; 7: 221
- 20 Brady WT, Saidi K. J. Org. Chem. 1980; 45: 727
- 21 Arya F, Bouquant J, Chuche J. Tetrahedron Lett. 1986; 27: 1913
- 22 Brady WT, Gu Y. J. Org. Chem. 1988; 53: 1353
- 23 France S, Wack H, Taggi AE, Hafez AM, Wagerle TR, Shah MH, Dusich CL, Lectka T. J. Am. Chem. Soc. 2004; 126: 4245
- 24 Bacchi S, Bongini A, Panunzio M, Villa M. Synlett 1998; 843
- 25 Müller M, Birner G, Dekant W. Chem. Res. Toxicol. 1998; 11: 454
- 26 Palomo C, Aizpurua JM, Ganboa I, Odriozola B, Urchegui R, Görls H. Chem. Commun. 1996; 1269
- 27 Sheehan JC, Henery-Logan KR. J. Am. Chem. Soc. 1957; 79: 1262
- 28 Woodward RB, Heusler K, Gosteli J, Naegeli P, Oppolzer W, Ramage R, Ranganathan S, Vorbrüggen H. J. Am. Chem. Soc. 1966; 88: 852
- 29 Yerxa BR, Moore HW. Tetrahedron Lett. 1992; 33: 7811
- 30 Merino I, Hegedus LS. Organometallics 1995; 14: 2522
- 31 Islami MR, Allen AD, Vukovic S, Tidwell TT. Org. Lett. 2011; 13: 494
- 32 Fu N, Allen AD, Chan W, Kobayashi S, Tidwell TT, Tahmassebi D, Aguilar A, Cabrera EP, Godoy J. Can. J. Chem. 2008; 86: 333
- 33 Gong L, McAllister MA, Tidwell TT. J. Am. Chem. Soc. 1991; 113: 6021
- 34 Tidwell TT. Ketenes . 2nd ed. John Wiley; Hoboken: 2006
- 35 Aguilar-Aguilar A, Allen AD, Peña-Cabrera E, Fedorov A, Fu N, Henry-Riyad H, Kobayashi S, Leuninger J, Schmid U, Tidwell TT, Verma R. J. Org. Chem. 2005; 70: 9556
- 36a Wang D, Nanding H, Han N, Chen F, Zhao G. J. Agric. Food Chem. 2008; 56: 1495
- 36b Gloede J, Poduska K, Gross H, Rudinger J. Collect. Czech. Chem. Commun. 1968; 33: 1307
- 37 Fu N, Tidwell TT. Tetrahedron 2008; 64: 10465
- 38 Jiao L, Liang Y, Xu J. J. Am. Chem. Soc. 2006; 128: 6060
- 39 Cossio FP, Ugalde JM, Lopez X, Lecea B, Palomo C. J. Am. Chem. Soc. 1993; 115: 995