Synthesis 2012; 44(12): 1849-1853
DOI: 10.1055/s-0031-1290946
special topic
© Georg Thieme Verlag Stuttgart · New York

A Novel Multicomponent Tandem Phosphine-Catalyzed Umpolung Reaction: Facile Access to Highly Functionalized α-Aminonitriles

Jian-Ming Chen
Department of Organic Chemistry, College of Chemistry, Jilin University, 2699 Qianjin Street, Changchun 130012, P. R. of China, Fax: +86(431)85153812   Email: wliao@jlu.edu.cn
,
Yin-Zhi Fang
Department of Organic Chemistry, College of Chemistry, Jilin University, 2699 Qianjin Street, Changchun 130012, P. R. of China, Fax: +86(431)85153812   Email: wliao@jlu.edu.cn
,
Zhong-lin Wei
Department of Organic Chemistry, College of Chemistry, Jilin University, 2699 Qianjin Street, Changchun 130012, P. R. of China, Fax: +86(431)85153812   Email: wliao@jlu.edu.cn
,
Wei-Wei Liao*
Department of Organic Chemistry, College of Chemistry, Jilin University, 2699 Qianjin Street, Changchun 130012, P. R. of China, Fax: +86(431)85153812   Email: wliao@jlu.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 27 February 2012

Accepted after revision: 07 March 2012

Publication Date:
20 April 2012 (eFirst)

Abstract

The first phosphine-catalyzed multicomponent tandem Strecker–γ-umpolung-addition reaction has been developed, which provides a facile access to functionalized allylic α-aminonitriles. The reaction is highly efficient, rapid, versatile and economical, and it is hoped that it will find great practical application in organic synthesis.

Supporting Information

 
  • References

    • For reviews, see:

    • 1a Lu X, Zhang C, Xu Z. Acc. Chem. Res. 2001; 34: 535
    • 1b Valentine DH, Hillhouse JH. Synthesis 2003; 317
    • 1c Methot JL, Roush WR. Adv. Synth. Catal. 2004; 346: 1035
    • 1d Lu X, Du Y, Lu C. Pure Appl. Chem. 2005; 77: 1985
    • 1e Nair V, Menon RS, Sreekanth AR, Abhilash N, Biju AT. Acc. Chem. Res. 2006; 39: 520
    • 1f Denmark SE, Beutner GL. Angew. Chem. Int. Ed. 2008; 47: 1560
    • 1g Ye L.-W, Zhou J, Tang Y. Chem. Soc. Rev. 2008; 37: 1140
    • 1h Kwong CK.-W, Fu MY, Lam CS.-L, Toy PH. Synthesis 2008; 2307
    • 1i Aroyan CE, Dermenci A, Miller SJ. Tetrahedron 2009; 65: 4069
    • 1j Cowen BJ, Miller SJ. Chem. Soc. Rev. 2009; 38: 3102
    • 1k Marinetti A, Voituriez A. Synlett 2010; 174
    • 1l Beata K. Cent. Eur. J. Chem. 2010; 1147
    • 2a Trost BM, Li C.-J. J. Am. Chem. Soc. 1994; 116: 3167
    • 2b Trost BM, Li C.-J. J. Am. Chem. Soc. 1994; 116: 10819
    • 2c Trost BM, Drake GR. J. Org. Chem. 1997; 62: 5670
    • For selected examples, see:

    • 3a Zhang C, Lu X. Synlett 1995; 645
    • 3b Chen Z, Zhu G, Jiang Q, Xiao D, Cao P, Zhang X. J. Org. Chem. 1998; 63: 5631
    • 3c Alvarez-Ibarra C, Csaky AG, Oliva CG. Tetrahedron Lett. 1999; 40: 8465
    • 3d Alvarez-Ibarra C, Csaky AG, Oliva CG. J. Org. Chem. 2000; 65: 3544
    • 3e Lu C, Lu X. Org. Lett. 2002; 4: 4677
    • 3f Pakulski Z, Demchuk OM, Frelek J, Luboradzki R, Pietrusiewicz KM. Eur. J. Org. Chem. 2004; 3913
    • 3g Virieux D, Guillouzic A.-F, Cristau H.-J. Tetrahedron 2006; 62: 3710
    • 3h Chung YK, Fu GC. Angew. Chem. Int. Ed. 2009; 48: 2225
    • 3i Smith SW, Fu GC. J. Am. Chem. Soc. 2009; 131: 14231
    • 3j Cardoso AL, Matos Beja A, Ramos Silva M, de los Santos JM, Palacios F, Abreu PE, Pais AA. C. C, Pinho e Melo TM. V. D. Tetrahedron 2010; 66: 7720
    • 3k Zhang Q, Yang L, Tong X. J. Am. Chem. Soc. 2010; 132: 2550
    • For examples of phosphine-catalyzed tandem reactions, see:

    • 4a Lu C, Lu X. Org. Lett. 2002; 4: 4677
    • 4b Gabillet S, Lecerclé D, Loreau O, Dézard S, Gomis J.-M, Taran F. Synthesis 2007; 515
    • 4c Guan X.-Y, Wei Y, Shi M. Org. Lett. 2010; 12: 5024
    • For selected reviews, see:

    • 5a Albright JD. Tetrahedron 1983; 39: 3207
    • 5b Enders D, Shilvock JP. Chem. Soc. Rev. 2000; 29: 359
    • 5c Opatz T. Synthesis 2009; 1941
    • For selected examples, see:

    • 6a Freifelder M, Hasbrouck RB. J. Am. Chem. Soc. 1960; 82: 696
    • 6b Gaiffe A, Padovani A. C. R. Acad. Sci., Ser. C 1969; 269: 144
    • 6c Enders D, Lotter H. Tetrahedron Lett. 1982; 23: 639
    • 6d Taillades J, Commeyras A. Tetrahedron 1974; 30: 127
    • Recent examples on quaternary α-aminonitrile synthesis via Strecker reaction:

    • 7a Rueping M, Sugiono E, Moreth SA. Adv. Synth. Catal. 2007; 349: 759
    • 7b Baeza A, Nájera C, Sansano JM. Synthesis 2007; 1230
    • 7c Abell JP, Yamamoto H. J. Am. Chem. Soc. 2009; 131: 15118
    • 7d Liu Y-L, Zhou F, Cao J-J, Ji C-B, Ding M, Zhou J. Org. Biomol. Chem. 2010; 8: 3847
    • 7e Zhang G-W, Zheng D.-H, Nie J, Wang T, Ma J.-A. Org. Biomol. Chem. 2010; 8: 1399
    • 8a Zhuang Z, Pan F, Fu J.-G, Chen J.-M, Liao W.-W. Org. Lett. 2011; 13: 6164
    • 8b Pan F, Chen J.-M, Zhuang Z, Fang Y.-Z, Zhang SX.-A, Liao W.-W. Org. Biomol. Chem. 2012; 10: 2214
  • 9 Wuts PG. M, Greene TW. Protective Groups in Organic Synthesis . 4th ed. Wiley; New York: 2007: 813-814