LiBr: A Mild Lewis Acid Catalyst for Efficient One-Pot Synthesis of α-Amino Nitriles

REFERENCES

• Singh , N. ; Sandhu , J. S. Studies in conjucated imines: Addition of cyanide ion to N-cinnamylidene aniline . Chem. Industry 1966 , 1415 .
   Google Scholar
• Harusaya , S. ; Hamada , Y. ; Shioiri , T. Diethyl phosphorocyanidated (DEPC): A novel reagent for the classical Strecker's α-amino nitrile synthesis . Tetrahedron Lett. 1979 , 20 , 4663 .
   Google Scholar
• Takamura , M. ; Hamashima , Y. ; Usuda , D. ; Kanai , M. ; Shibasaki , M. A catalytic asymmetric strecker-type reaction: Interesting reactivity difference between TMSCN and HCN. Angew. Chem. Int. Ed. 2000, 39, 1650; (b) Sigman , M. S. ; Jacobsen , E. N. Enantioselective addition of hydrogen cyanide to imines catalyzed by a chiral (Salen)Al(III) complex. J. Am. Chem. Soc. 1998, 120, 5315.
   PubMed Web of Science ®Google Scholar
• Paraskar , A. S. ; Sudalai , A. Cu(OTf)2 or Et3N-catalyzed three-component condensation of aldehydes, amines, and cyanides: A high yielding synthesis of α-aminonitriles . Tetrahedron Lett. 2006 , 47 , 5759 .
   Web of Science ®Google Scholar
• Shaabani , A. ; Maleki , A. Cellulose sulfuric acid as a bio-supported and recyclable solid acid catalyst for the one-pot three-component synthesis of α-amino nitriles . Appl. Catal. A: General 2007 , 331 , 149 .
   Web of Science ®Google Scholar
• Chen , W. -Y. ; Lu , J. Silica sulfuric acid catalyzed one-pot synthesis of α-aminonitriles . Synlett 2005 , 2293 ; (b) Heydari , A. ; Khaksar , S. ; Pourayoubi , M. ; Mahjoub , A. R. Sulfamic acid: An efficient, cost-effective, and recyclable solid acid catalyst for the three-component synthesis of α-amino nitriles . Tetrahedron Lett. 2007 , 48 , 4059 ; (c) Mulzer , J. ; Meier , A. ; Buschmann , J. ; Luger , P. Synthesis of enantiopure 1,2-didehydropyrrolidine, d-proline, and oxazoline derivatives via staudinger–aza–wittig cyclization of γ-azido aldehydes . Synthesis 1996 , 123 ; (d) De , S. K. RuCl3 catalyzed one-pot synthesis of α-aminonitriles . Synth. Commun. 2005 , 35 , 653 ; (e) De , S. K. Vanadyl triflate as an efficient and recyclable catalyst for the synthesis of α-Aminonitriles . Synth. Commun. 2005 , 35 , 1577 ; (f) Narasimhulu , M. ; Reddy , T. S. ; Mahesh , K. C. ; Reddy , S. M. ; Reddy , A. V. ; Venkateswarlu , Y. Lanthanum(III) nitrate hexahydrate or gadolinium(III) chloride hexahydrate catalyzed one-pot synthesis of α-amino nitriles . J. Mol. Catal. A: Chemical 2007 , 264 , 288 .
   Google Scholar
• Laskar , D. D. ; Prajapti , D. ; Sandhu , J. S. Lithium bromide catalyzed ehrlich-sachs reactions using solvent-free conditions . Synth. Commun. 2001 , 31 , 1427 ; (b) Baruah , P. P. ; Gadhwal , S. ; Prajapati , D. ; Sandhu , J. S. The biginelli condensation: A novel and efficient regioselective synthesis of dihydropyrimidin-2(1H)-ones using lithium bromide . Chem. Lett. , 2002 , 1038 ; (c) Saini , A. ; Kumar , S. ; Sandhu , J. S. A new libr-catalyzed, facile and efficient method for the synthesis of 14-alkyl or aryl-14H-dibenzo[a,j]xanthenes and tetrahydrobenzo[b]pyrans under solvent-free conventional and microwave heating . Synlett 2006 , 1928 ; (d) Ono , F. ; Negoro , R. ; Sato , T. Lithium bromide, a novel and highly effective catalyst for monothioacetalization of acetals under mild reaction conditions . Synlett 2001 , 1581 ; (e) Seeback , D. ; Thaler , A. ; Blaser , D. ; Ko , S. Y. Transesterifications with 1,8-diazabicyclo[5.4.0]undec-7-ene/lithium bromide (DBU/LiBr)—Also applicable to cleavage of peptides from resins in Merrifleld syntheses . Helv. Chem. Acta 1991 , 74 , 1102 .
   Web of Science ®Google Scholar
• Firouzabadi , H. ; Karimi , M. ; Eslami , S. Lithium trifluoromethanesulfonate (LiOTf) as a highly efficient catalyst for chemoselective dithioacetalization of carbonyl compounds under neutral and solvent-free conditions . Tetrahedron Lett. 1999 , 40 , 4055 .
   Web of Science ®Google Scholar
• Yanovskya , L. A. ; Shachidayatov , C. ; Kutcherav , V. E. The reaction of cyanohydrins with α,β-unsaturated aldehydes. Tetrahedron 1967, 23, 1311.
   Google Scholar
• El-Ahl , A. -A. S. A novel uncatalyzed insertion reaction of in situ formed trichlorosilyl cyanide with imines: A facile silicon mediated synthesis of α-aminonitriles . Synth. Commun. 2003 , 33 , 989 ; (b) Sandhu , J. S. ; Mohan , S. ; Sethi , P. S. Oxidation of cinnamylaryl amine with manganese dioxide . Chem. Ind. 1970 , 52 , 1658 ; (c) Walia , J. S. ; Rao , D. H. Structure of the product obtained in the reaction of N-cinnamylidene aniline with cyanide ion . Indian J. Chem. 1965 , 3 , 327 .
   Web of Science ®Google Scholar