Download PDF
Synlett 2011(9): 1262-1264  
DOI: 10.1055/s-0030-1259956
CLUSTER
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Synthesis of 2-Aryl-3-nitro-2H-chromenes Catalyzed by a Bifunctional Thiourea

Zhiguo Zhang, Gergely Jakab, Peter R. Schreiner*
Institut für Organische Chemie, Justus-Liebig-Universität Gießen, Heinrich-Buff-Ring 58, 35392 Giessen, Germany
Fax: +49(641)9934309; e-Mail: prs@org.chemie.uni-gießen.de;
Further Information

Publication History

Received 2 February 2011
Publication Date:
20 April 2011 (online)

    Permissions and Reprints All articles of this category

Abstract

A bifunctional thiourea-catalyzed tandem approach of oxa-Michael-aza-Henry-desulfonamidation was used to synthesize chiral 2-aryl-3-nitro-2H-chromenes. This method provides direct access to the corresponding products in moderate to good yields and enantioselectivities.

Key words

bifunctional organocatalysis - H bond - nitrochromene - tandem reaction - thiourea

    References

  • 1a Johansson L. Sohn D. Thorberg S.-O. Jackson DM. Kelder D. Larsson L.-G. Rényi L. Ross SB. Wallsten C. Eriksson H. Hu P.-S. Jerning E. Mohell N. Westlind-Danielsson A. J. Pharmacol. Exp. Ther.  1997,  283:  216 
    Google Scholar
  • 1b Rene L. Royer R. Eur. J. Med. Chem.  1982,  89 
    Google Scholar
  • 1c Rene L. Blanco L. Royer R. Cavier R. Lemoine J. Eur. J. Med. Chem.  1977,  385 
    Google Scholar
  • 1d Muruganantham R. Mobin SM. Namboothiri INN. Org. Lett.  2007,  9:  1125 
    Google Scholar
  • 1e Kolokythas G. Kostakis IK. Pouli N. Marakos P. Kousidou OC. Tzanakakis GN. Karamanos NK. Eur. J. Med. Chem.  2007,  307 
    Google Scholar
  • 1f Furuta T. Hirooka Y. Abe A. Sugata Y. Ueda M. Murakami K. Suzuki T. Tanaka K. Kan T. Bioorg. Med. Chem. Lett.  2007,  17:  3095 
    Google Scholar
  • 1g Perrella FW. Chen S.-F. Behrens DL. Kaltenbach RF. Seitz SP. J. Med. Chem.  1994,  37:  2232 
    Google Scholar
  • 1h Moreau C. Gally F. Jacquet-Bouix H. Vivaudou M. Mol. Pharmacol.  2005,  67:  1026 
    Google Scholar
  • 1i Cueva JP. Giorgioni G. Grubbs RA. Chemel BR. Watts VJ. Nichols DE. J. Med. Chem.  2006,  49:  6848 
    Google Scholar
  • 1j Mori J. Iwashima M. Takeuchi M. Saito H. Chem. Pharm. Bull.  2006,  54:  391 
    Google Scholar
  • 1k Kashiwada Y. Yamazaki K. Ikeshiro Y. Yamagishi T. Fujioka T. Mihashi K. Mizuki K. Cosentino LM. Fowke K. Morris-Natschke SL. Lee K.-H. Tetrahedron  2001,  57:  1559 
    Google Scholar
  • 1l Nicolaou KC. Pfefferkorn JA. Roecker AJ. Cao GQ. Barluenga S. Mitchell HJ. J. Am. Chem. Soc.  2000,  122:  9939 
    Google Scholar
  • 1m Mannhold R. Cruciani G. Weber H. Lemoine H. Derix A. Weichel C. Clementi M. J. Med. Chem.  1999,  42:  981 
    Google Scholar
  • 1n Iwasaki T. Mihara S. Shimamura T. Kawakami M. Masui M. Hayasaki-Kajiwara Y. Naya N. Ninomiya M. Fujimoto M. Nakajima M. J. Cardiovasc. Pharm.  2001,  37:  471 
    Google Scholar
  • 2a Xu DQ. Wang YF. Luo SP. Zhang S. Zhong AG. Chen H. Xu ZY. Adv. Synth. Catal.  2008,  350:  2610 
    Google Scholar
  • 2b Karthikeyan T. Sankararaman S. Tetrahedron: Asymmetry  2008,  19:  2741 
    Google Scholar
  • 3 Xie JW. Fan LP. Su H. Li XS. Xu DC. Org. Biomol. Chem.  2010,  8:  2117 
    CrossrefGoogle Scholar
  • 4a Zhang ZG. Schreiner PR. Chem. Soc. Rev.  2009,  38:  1187 
    Google Scholar
  • 4b Kotke M. Schreiner PR. (Thio)urea Organocatalysis, In Hydrogen Bonding in Organic Synthesis   Pihko P. Wiley-VCH; Weinheim: 2009. 
    Google Scholar
  • 4c Doyle AG. Jacobsen EN. Chem. Rev.  2007,  107:  5713 
    Google Scholar
  • 4d Taylor MS. Jacobsen EN. Angew. Chem. Int. Ed.  2006,  45:  1520 
    Google Scholar
  • 4e Takemoto Y. Org. Biomol. Chem.  2005,  3:  4299 
    Google Scholar
  • 4f Akiyama T. Itoh J. Fuchibe K. Adv. Synth. Catal.  2006,  348:  999 
    Google Scholar
  • 4g Berkessel A. Gröger H. Asymmetric Organocatalysis: From Biomimetic Concepts to Applications in Asymmetric Synthesis   Wiley-VCH; Weinheim: 2005. 
    Google Scholar
  • 5 Connon SJ. Chem. Commun.  2008,  2499 
    Google Scholar
  • 6a Vakulya B. Varga S. Csámpai A. Soós T. Org. Lett.  2005,  7:  1967 
    Google Scholar
  • 6b McCooey SH. Connon SJ. Angew. Chem. Int. Ed.  2005,  44:  6367 
    Google Scholar
  • 7a Zhang ZG. Schreiner PR. Synthesis  2007,  2559 
    Google Scholar
  • 7b Zhang ZG. Schreiner PR. Synlett  2007,  1455 
    Google Scholar
  • 7c Weil T. Kotke M. Kleiner CM. Schreiner PR. Org. Lett.  2008,  10:  1513 
    Google Scholar
  • 7d Kotke M. Schreiner PR. Synthesis  2007,  779 
    Google Scholar
  • 7e Kotke M. Schreiner PR. Tetrahedron  2006,  62:  434 
    Google Scholar
  • 7f Kleiner CM. Schreiner PR. Chem. Commun.  2006,  4315 
    Google Scholar
  • 8 Sakakibara T. Koezuka M. Sudoh R. Bull. Chem. Soc. Jpn.  1978,  51:  3095 
    CrossrefGoogle Scholar
  • 9 Nielsen M. Jacobsen CB. Holub N. Paixão MW. Jørgensen KA. Angew. Chem. Int. Ed.  2010,  49:  2668 
    CrossrefPubMedGoogle Scholar