Synthesis 2013; 45(12): 1654-1658
DOI: 10.1055/s-0033-1338434
special topic
© Georg Thieme Verlag Stuttgart · New York

Highly Enantioselective Michael Addition of α-Substituted Nitrophosphonates to a Vinyl Sulfone

Guo-Ying Chen
Department of Chemistry & Medicinal Chemistry Program, Life Sciences Institute, National University of Singapore, 3 Science Drive 3, Singapore 117543, Republic of Singapore   Fax: +65(6779)1691   eMail: chmlyx@nus.edu.sg
,
Yixin Lu*
Department of Chemistry & Medicinal Chemistry Program, Life Sciences Institute, National University of Singapore, 3 Science Drive 3, Singapore 117543, Republic of Singapore   Fax: +65(6779)1691   eMail: chmlyx@nus.edu.sg
› Institutsangaben
Weitere Informationen

Publikationsverlauf

Received: 08. März 2013

Accepted after revision: 02. April 2013

Publikationsdatum:
17. April 2013 (online)

Abstract

Organocatalytic asymmetric Michael reaction of α-substituted nitrophosphonates to phenyl vinyl sulfone catalyzed by cinchona alkaloid-derived tertiary amine-thioureas afforded α,α-disubstituted nitrophosphonates in very good yields and excellent enantiomeric excesses.

Supporting Information

 
  • References

    • 1a Chavane V. Bull. Soc. Chim. Fr. 1948; 15: 774
    • 1b Kudzin ZH, Kudzin MH, Drabowicz J, Stevens CV. Curr. Org. Chem. 2011; 15: 2015
    • 1c Orsini F, Sello G, Sisti M. Curr. Med. Chem. 2010; 17: 264
    • 1d Smith III AB, Yager KM, Taylor CM. J. Am. Chem. Soc. 1995; 117: 10879

      For selected articles, see:
    • 2a Allen JG, Atherton FR, Hall MJ, Hassall CH, Holmes SW, Lambert RW, Nisbet LJ, Ringrose PS. Nature 1978; 272: 56
    • 2b Atherton FR, Hassall CH, Lambert RW. J. Med. Chem. 1986; 29: 29
    • 2c Pratt RF. Science 1989; 246: 917
    • 2d Maier L, Diel PJ. Phosphorus Sulfur Silicon 1991; 57: 57
    • 2e Kaplan AP, Bartlett PA. Biochemistry 1991; 30: 8165
    • 2f Hirschmann R, Smith III AB, Taylor CM, Benkovic PA, Taylor SD, Yager KM, Sprengler PA, Benkovics SJ. Science 1994; 265: 234
    • 2g Alonso E, Solis A, del Pozo C. Synlett 2000; 698
    • 2h Sienczyk M, Oleksyszyn J. Curr. Med. Chem. 2009; 16: 1673
    • 2i Mucha A, Kafarski P, Berlicki Ł. J. Med. Chem. 2011; 54: 5955

      For selected examples, see:
    • 3a Ma J. Chem. Soc. Rev. 2006; 35: 630
    • 3b Merino P, Marques-Lopez E, Herrera RP. Adv. Synth. Catal. 2008; 350: 1195
    • 3c Schlemminge I, Saida Y, Groeger H, Maison W, Durot N, Sasai H, Shibasaki M, Martens J. J. Org. Chem. 2000; 65: 4818
    • 3d Joly GD, Jacobsen EN. J. Am. Chem. Soc. 2004; 126: 4102
    • 3e Saito B, Egami H, Katsuki T. J. Am. Chem. Soc. 2007; 129: 1978
    • 3f Kiyohara H, Nakamura Y, Matsubara R, Kobayashi S. Angew. Chem. Int. Ed. 2006; 45: 1615
    • 3g Dodda R, Zhao C.-G. Tetrahedron Lett. 2007; 48: 4339
    • 3h Bernardi L, Zhuang W, Jørgensen AK. J. Am. Chem. Soc. 2005; 127: 5772
    • 3i Kim MS, Hye RK, Kim YD. Org. Lett. 2005; 7: 2309
    • 3j Kuwano R, Nishio R, Ito Y. Org. Lett. 1999; 1: 837
    • 3k Reddy MV. N, Balakrishna A, Kumar MA, Reddy GC. S, Sankar AU. R, Reddy CS, Krishna TM. Chem. Pharm. Bull. 2009; 57: 1391
  • 4 Wilt JC, Pink M, Johnston JN. Chem. Commun. 2008; 4177
  • 5 Bera K, Namboothiri IN. N. Org. Lett. 2012; 14: 980
  • 6 Tripathi CB, Kayal S, Mukherjee S. Org. Lett. 2012; 14: 3296

    • For reviews, see:
    • 7a Nielsen M, Jacobsen CB, Holub N, Paixão MW, Jørgensen KA. Angew. Chem. Int. Ed. 2010; 49: 2668
    • 7b Zhu Q, Lu Y. Aust. J. Chem. 2009; 62: 951

    • For recent examples, see:
    • 7c Li H, Song J, Liu X, Deng L. J. Am. Chem. Soc. 2005; 127: 8948
    • 7d Li H, Song J, Deng L. Tetrahedron 2009; 65: 3139
    • 7e Mossé S, Alexakis A. Org. Lett. 2005; 7: 4361
    • 7f Quintard A, Bournaud C, Alexakis A. Chem. Eur. J. 2008; 14: 7504
    • 7g Quintard A, Alexakis A. Chem. Eur. J. 2009; 15: 11109
    • 7h Sulzer-Mossé S, Alexakis A, Mareda J, Bollot G, Bernardinelli G, Filinchuk Y. Chem. Eur. J. 2009; 15: 3204
    • 7i Quintard A, Belot S, Sebastien M, Marchal E, Alexakis A. Eur. J. Org. Chem. 2010; 927
    • 7j Quintard A, Alexakis A. Chem. Commun. 2010; 46: 4085
    • 7k Landa A, Maestro M, Masdeu C, Puente A, Vera S, Oiarbide M, Palomo C. Chem. Eur. J. 2009; 15: 1562
    • 7l Liu T.-Y, Long J, Li B.-J, Jiang L, Li R, Wu Y, Ding L.-S, Chen Y.-C. Org. Biomol. Chem. 2006; 4: 2097
    • 7m Alba A.-NR, Companyo X, Valero G, Moyano A, Rios R. Chem. Eur. J. 2010; 16: 5354
    • 8a Zhu Q, Lu Y. Org. Lett. 2008; 10: 4803
    • 8b Zhu Q, Cheng L, Lu Y. Chem. Commun. 2008; 6315
    • 8c Zhu Q, Lu Y. Org. Lett. 2009; 11: 1721
    • 8d Zhu Q, Lu Y. Chem. Commun. 2010; 46: 2235
    • 8e Zhu Q, Lu Y. Angew. Chem. Int. Ed. 2010; 49: 7753
  • 9 Han X, Zhong F, Lu Y. Adv. Synth. Catal. 2010; 352: 2778
  • 10 CCDC 926461 contains the supplementary crystallographic data for 3a, which can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif or by writing to the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; Fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk.
  • 11 Vakulya B, Varga S, Csámpai A, Soós T. Org. Lett. 2005; 7: 1976