Uncatalyzed Addition of TMSCN to Acylphosphonates

Abstract

The cyanosilylations of various alkyl- and arylphosphonates under comparatively mild conditions furnished the trimethylsilyloxycyanophosphonates in high yield. The addition to ketophosphonate functions works without the influence of a catalyst.

Key words

cyanohydrins - addition reactions - phosphorus - nucleophilic additions

References

• 1a Gregory RJH. Chem. Rev.  1999,  99:  3649 
• 1b North M. Tetrahedron: Asymmetry  2003,  14:  147 
• 1c Brunel J.-M. Holmes IP. Angew. Chem. Int. Ed.  2004,  43:  2752 
• 1d Kim SS. Kwak JM. Tetrahedron  2006,  62:  49 
• 1e Liu X. Qin B. Zhou X. He B. Feng X. J. Am. Chem. Soc.  2005,  127:  12224 
• For reviews on construction of quaternary stereocenters, see:
• 1f Fuji K. Chem. Rev.  1993,  93:  2037 
• 1g Corey EJ. Guzmanperez A. Angew. Chem. Int. Ed.  1998,  37:  388 
• 1h Christoffers J. Mann A. Angew. Chem. Int. Ed.  2001,  40:  4591 
• 2a Matthews BR. Gountzos H. Jackson WR. Watson KG. Tetrahedron Lett.  1989,  30:  5157 
• 2b Ziegler T. Horsch B. Effenberger F. Synthesis  1990,  575 
• 2c Effenberger F. Stelzer U. Angew. Chem., Int. Ed. Engl.  1991,  30:  873 
• 2d Belokon YN. Green B. Ikonnikov NS. North M. Tararov VI. Tetrahedron Lett.  1999,  40:  8147 
• 2e Belokon YN. Green B. Ikonnikov NS. North M. Parsons T. Tararov VI. Tetrahedron  2001,  57:  771 
• 2f Gröger H. Chem. Rev.  2003,  103:  2795 
• 3a Evans DA. Sarroll GL. Truesdale LK. J. Org. Chem.  1974,  39:  914 
• 3b Evans DA. Truesdale LK. Tetrahedron Lett.  1973,  14:  4929 
• 3c Okino T. Hoashi Y. Takemoto Y. Tetrahedron Lett.  2003,  44:  2817 
• 4 North M. Synlett  1993,  807 
• 5a For organocatalytical additions of carbon nucleophiles to acyl phosphonates, see: Reis O. PhD Thesis   Middle East Technical University; Ankara: 2005. 
• 5b Samanta S. Zhao C.-G. J. Am. Chem. Soc.  2006,  128:  7442 
• 6a Konovalova IV. Burnaeva LA. Saifullina NS. Pudovik AN. Zh. Obshch. Khim.  1976,  46:  18 
• 6b Lebedev EP. Pudovik AN. Tsyganov BN. Nazmutdinov RY. Romanov GV. Zh. Obshch. Khim.  1977,  47:  765 
• 7 Kazantsev AV. Averin AD. Lukashev NV. Beletskaya IP. Russ. J. Org. Chem.  1998,  34:  1432 
• 8 Demir AS. Reis O. Igdir AC. Esiringu I. Eymur S. J. Org Chem.  2005,  70:  10584 
• 9 Shibasaki M. Kanai M. Funabashi K. Chem. Commun.  2002,  1989 
• 10 Ryu DH. Corey EJ. J. Am. Chem. Soc.  2004,  126:  8106 ; and references cited therein