Strecker Reaction of Aldimines Catalyzed by a Nucleophilic N-Heterocyclic Carbene

Abstract

The first method for Strecker reaction (cyanation of imines) of aldimines with TMSCN in the presence of N-heterocyclic carbene prepared from 1,3-bis(2,4,6-trimethylphenyl)imidazolium chloride and t-BuOK, as a nucleophilic catalyst, is described.

Key words

Strecker reaction - aldimine - N-heterocyclic carbene - imidazolium salt - cyanation

References

• For reviews, see:
• 1a César V. Bellemin-Laponnaz S. Gade LH. Chem. Soc. Rev.  2004,  33:  619 
• 1b Herrmann WA. Angew. Chem. Int. Ed.  2002,  41:  1291 
• For reviews, see:
• 2a Nair V. Bindu S. Sreekumar V. Angew. Chem. Int. Ed.  2004,  43:  5130 
• 2b Grasa GA. Singh R. Nolan SP. Synthesis  2004,  971 
• For examples, see:
• 2c Connor EF. Nyce GW. Myers M. Möck A. Hedrick JL. J. Am. Chem. Soc.  2002,  124:  914 
• 2d Grasa GA. Kissling RM. Nolan SP. Org. Lett.  2002,  4:  3583 
• 2e Suzuki Y. Toyota T. Imada F. Sato M. Miyashita A. Chem. Commun.  2003,  1314 
• 2f Singh R. Kissling RM. Letellier M.-A. Nolan SP. J. Org. Chem.  2004,  69:  209 
• 2g Sohn SS. Rosen EL. Bode JW. J. Am. Chem. Soc.  2004,  126:  14370 
• 2h Burstein C. Glorius F. Angew. Chem. Int. Ed.  2004,  43:  6205 
• 2i Kano T. Sasaki K. Maruoka K. Org. Lett.  2005,  7:  1347 
• 2j Ye W. Cai G. Zhuang Z. Jia X. Zhai H. Org. Lett.  2005,  7:  3769 
• Cyanosilylation of aldehyde:
• 3a Fukuda Y. Maeda Y. Ishii S. Kondo K. Aoyama T. Synthesis  2006,  589 
• Cyanophosphorylation of aldehyde:
• 3b Fukuda Y. Maeda Y. Kondo K. Aoyama T. Chem. Pharm. Bull.  2006,  54:  397 
• For reviews, see:
• 4a Gröger H. Chem. Rev.  2003,  103:  2795 
• 4b Yet L. Angew. Chem. Int. Ed.  2001,  40:  875 
• 5 Bode has reported that carbene 2 reacts irreversibly with N-(4-bromobenzylidene)-4-methylbenzenesulfonamide in CD₃OD at r.t.: He M. Bode JW. Org. Lett.  2005,  7:  3131 
• Selected recent examples:
• 6a Takamura M. Hamashima Y. Usuda H. Kanai M. Shibasaki M. Angew. Chem. Int. Ed.  2000,  39:  1650 
• 6b Takamura M. Hamashima Y. Usuda H. Kanai M. Shibasaki M. Chem. Pharm. Bull.  2000,  48:  1586 
• 6c Huang J. Corey EJ. Org. Lett.  2005,  6:  5027 
• 6d Banphavichit V. Mansawat W. Bhanthumnavin W. Vilaivan T. Tetrahedron  2004,  60:  10559 
• 6e Nakamura S. Sato N. Sugimoto M. Toru T. Tetrahedron: Asymmetry  2004,  15:  1513 
• 6f Jiao Z. Feng X. Liu B. Chen F. Zhang G. Jiang Y. Eur. J. Org. Chem.  2003,  3818 
• 6g Mansawat W. Bhanthumnavin W. Vilaivan T. Tetrahedron Lett.  2003,  44:  3805 
• 7 Jennings WB. Lovely CJ. Tetrahedron Lett.  1988,  29:  3725