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.

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