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

Guo-Ying Chen; Yixin Lu

doi:10.1055/s-0033-1338434

Synthesis, Table of Contents

Synthesis 2013; 45(12): 1654-1658
DOI: 10.1055/s-0033-1338434

special topic

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

› Author Affiliations

Abstract

All articles of this category

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.

Key words

thiourea - Michael Addition - cinchona alkaloid - vinyl sulfone - nitrophosphonate

Full Text

References

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

Supplementary Material

Supporting Information