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 2014; 25(11): 1555-1560
DOI: 10.1055/s-0033-1341275
DOI: 10.1055/s-0033-1341275
letter
Studies of the New Reactivity of Chiral Acrylamides and Unprotected Pyrroles: Diastereoselective and Carbonyl Compatible 1,4-Addition
Further Information
Publication History
Received: 05 March 2014
Accepted after revision: 31 March 2014
Publication Date:
13 May 2014 (online)
![](https://www.thieme-connect.de/media/synlett/201411/lookinside/thumbnails/10.1055-s-0033-1341275-1.jpg)
Abstract
A diversity of new functionalized cyclic and acyclic chiral pyrroloamides compounds were synthesized in good yields and diastereoselectivities in the case of cyclic pyrroloamides. This simple and robust process involves the creation of a C–C bond between unprotected pyrroles and cyclic or hindered chiral acrylamides.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000083.
- Supporting Information
-
References and Notes
- 1a Friedel C, Crafts JM. Hebd. Seances Acad. Sci. 1877; 84: 1392
- 1b Friedel C, Crafts JM. Hebd. Seances Acad. Sci. 1877; 84: 1450
- 1c Olah GA. Friedel Crafts and Related Reactions . Vol. II. Wiley-Interscience; New York: 1964: Part 1
- 1d Roberts RM, Khalaf AA. Friedel-Crafts Alkylation Chemistry: A Century of Discovery . Dekker; New York: 1984
- 1e Olah GA, Krishnamurti R, Prakash GK. S. Friedel-Crafts Alkylations in Comprehensive Organic Synthesis . Pergamon Press; Oxford: 1991
- 2a Catalytic Asymmetric Friedel–Crafts Alkylations . Bandini M, Umani-Ronchi A. Wiley-VCH; Weinheim: 2009: 1-301
- 2b Poulsen TB, Jørgensen KA. Chem. Rev. 2008; 108: 2903
- 3a Zhuang W, Gathergood N, Hazell RG, Jørgensen KA. J. Org. Chem. 2001; 66: 1009
- 3b Yadav JS, Abraham S, Subba Reddy BV, Sabitha G. Tetrahedron Lett. 2001; 42: 8063
- 3c Srivastava N, Banik BK. J. Org. Chem. 2003; 68: 2109
- 3d Palomo C, Oiarbide M, Kardak BG, Garcia JM, Linden A. J. Am. Chem. Soc. 2005; 127: 4154
- 3e Kusurkar RS, Nayak SK, Chavan NL. Tetrahedron Lett. 2006; 47: 7323
- 3f Blay G, Fernandez I, Pedro JR, Vila C. Org. Lett. 2007; 9: 2601
- 3g Evans DA, Fandrick KR, Song HJ, Scheidt KA, Xu RS. J. Am. Chem. Soc. 2007; 129: 10029
- 3h Sibi MP, Coulomb J, Stanley LM. Angew. Chem. Int. Ed. 2008; 47: 9913
- 3i Trost BM, Müller C. J. Am. Chem. Soc. 2008; 130: 2438
- 3j Huang Y, Tokunaga E, Suzuki S, Shiro M, Shibata N. Org Lett. 2010; 12: 1136
- 4a Fürstner A. Angew. Chem. Int. Ed. 2003; 42: 3582
- 4b Hoffmann H, Lindel T. Synthesis 2003; 1753
- 4c Balme G. Angew. Chem. Int. Ed. 2004; 43: 6238
- 4d Jolicoeur B, Chapman EE, Thompson A, Lubell WD. Tetrahedron 2006; 62: 11531
- 4e Trofimo NA, Nedolya NA In Comprehensive Heterocyclic Chemistry III . Vol. 3. Katritzky AR, Ramsden CA, Scriven EF. V, Taylor RJ. K. Elsevier Ltd; Oxford: 2008: 45-268
- 4f Lipshutz BH. Chem. Rev. 1986; 86: 795
- 5a Trost BM, Müller C. J. Am. Chem. Soc. 2008; 130: 2438
- 5b Blay G, Fernandez I, Pedro JR, Vila C. Org. Lett. 2007; 9: 2601
- 5c Evans DA, Fandrick KR, Song HJ, Scheidt KA, Xu RS. J. Am. Chem. Soc. 2007; 129: 10029
- 5d Palomo C, Oiarbide M, Kardak BG, Garcia JM, Linden A. J. Am. Chem. Soc. 2005; 127: 4154
- 5e Zhuang W, Gathergood N, Hazell RG, Jørgensen KA. J. Org. Chem. 2001; 66: 1009
- 5f George J, Reddy BV. S. Org. Biomol. Chem. 2012; 10: 4731
- 6 Kobayashi S, Busujima T, Nagayama S. Chem. Eur. J. 2000; 6: 3491
- 7 Nigst TA, Westermaier M, Ofial AR, Mayr H. Eur. J. Org. Chem. 2008; 2369
- 8a Chen I.-L, Wang T.-C, Chen Y.-L, Tzeng C.-C. J. Chin. Chem. Soc. 2000; 47: 155
- 8b Mazet C, Jacobsen EN. Angew. Chem. Int. Ed. 2008; 47: 1762
- 8c Tanaka Y, Kanai M, Shibasaki M. J. Am. Chem. Soc. 2010; 132: 8862
- 9a Gao J.-R, Wu H, Yiang B, Yu W.-B, Han L, Jia Y.-X. J. Am. Chem. Soc. 2013; 135: 2983
- 9b Wu H, Liu R.-R, Jia Y.-X. Synlett 2014; 25: 457
- 10a Enz A, Feuerbach D, Frederiksen MU, Gentsch C, Hurth K, Muller W, Nozulak J, Roy BL. Bioorg. Med. Chem. Lett. 2009; 19: 1287
- 10b Trabocchi A, Guarna F, Guarna A. Curr. Org. Chem. 2005; 9: 1127
- 10c Ordonez M, Cativiela C. Tetrahedron: Asymmetry 2007; 18: 3
- 11a Corey EJ, Zhang FY. Org. Lett. 2000; 2: 4257
- 11b Thakur VV, Nikalje MD, Sudalai A. Tetrahedron: Asymmetry 2003; 14: 581
- 11c Becht JM, Meyer O, Helmchen G. Synthesis 2003; 2805
- 11d Craig D, Hyland CJ. T, Ward SE. Chem. Commun. 2005; 3439
- 11e Enders D, Niemeier O. Heterocycles 2005; 66: 385
- 11f Paraskar AS, Sudalai A. Tetrahedron 2006; 62: 4907
- 11g Wee AG. H, Duncan SC, Fan G.-J. Tetrahedron: Asymmetry 2006; 17: 297
- 11h Hynes PS, Stupple PA, Dixon DJ. Org. Lett. 2008; 10: 1389
- 11i Bantreil X, Prestat G, Madec D, Fristrup P, Poli G. Synlett 2009; 1441
- 11j Wang J, Li W, Liu YL, Chu YY, Lin LL, Liu XH, Feng XM. Org. Lett. 2010; 12: 1280
- 12 Compounds 14–20 were synthesized by Ring-Closing Metathesis at room temperature (Scheme 7). The role of allyltrimethylsilane is to activate the catalytic cycle. These results will be published in the future: Gratais A., Bouzbouz S. unpublished work.
- 13a Johnson TA, Curtis MD, Beak PJ. J. Am. Chem. Soc. 2001; 123: 1004
- 13b Liu LT, Hong PC, Huang HL, Chen SF, Jeff Wang CL, Wen YS. Tetrahedron: Asymmetry 2001; 12: 419
- 13c Johnson TA, Jang DO, Slafer BW, Curtis MD, Beak PJ. J. Am. Chem. Soc. 2002; 124: 11689
- 13d Greenhalgh DA, Simpkins NS. Synlett 2002; 2074
- 13e Hughes G, Kimura M, Buchwald SL. J. Am. Chem. Soc. 2003; 125: 11253
- 13f Takasu K, Nishida N, Tomimura A, Ihara M. J. Org. Chem. 2005; 70: 3957
- 13g Brandau S, Landa A, Franzen J, Marigo M, Jøgensen KA. Angew. Chem. Int. Ed. 2006; 45: 4305
- 13h Bower JF, Riis-Johannessen T, Szeto P, Whitehead AJ, Gallagher T. Chem. Commun. 2007; 728
- 13i Hynes PS, Stupples PA, Dixon DJ. Org. Lett. 2008; 10: 1389
- 13j Kim M.-H, Park Y, Jeong BS, Park HG, Jew SS. Org. Lett. 2010; 12: 2826
- 13k Rupniak NM. J, White JF. Int. Patent WO 2010009316, 2010
- 13l Číhalová S, Valero G, Schimer J, Humpl M, Dračínský M, Moyano A, Rios R, Vesely J. Tetrahedron 2011; 67: 8942
- 14a Senda AT, Ogasawara M, Hayashi TJ. Org. Chem. 2001; 66: 6852
- 14b Gini F, Hessen B, Feringa BL, Minnaard A. J. Chem. Commun. 2007; 43: 710
- 14c Smith AJ, Abbott LK, Martin SF. Org. Lett. 2009; 11: 4200
- 14d Jin SS, Wang H, Xu MH. Chem. Commun. 2011; 47: 7230
- 14e Jin SS, Wang H, Zhu TS, Xu MH. Org. Biomol. Chem. 2012; 10: 1764
- 14f He ZT, Wei YB, Yu HJ, Sun CY, Feng CG, Tian P, Lin GQ. Tetrahedron 2012; 68: 9186
- 14g Cottet P, Müller D, Alexakis A. Org. Lett. 2013; 15: 828
- 15 Compounds 32–34 were synthesized by classical peptidic coupling sequence from Boc-Leu-OH or Boc-Phe-OH.
For reviews of Friedel–Crafts alkylation reactions, see:
For reviews on asymmetric FC reaction, see:
For selected examples of asymmetric FC reaction of unprotected pyrrole, see: