Synthetic application of in situ generation of N-acyliminium ions from α-amido p-tolylsulfones for the synthesis of α-amino nitriles
ST Kadam, P Thirupathi, SS Kim
Index: Kadam, Santosh T.; Thirupathi, Ponnaboina; Kim, Sung Soo Tetrahedron, 2010 , vol. 66, # 9 p. 1684 - 1688
Full Text: HTML
Citation Number: 8
Abstract
In the presence of catalytic amount of bismuth bromide (5mol%) the α-amido p-tolylsulfones are converted into N-acyliminium ions, which undergo the nucleophilic addition of trimethylsilyl cyanide (TMSCN) to provide the N-protected α-amino nitriles in very good yield. A variety of α-amido p-tolylsulfones were prepared from aromatic as well as aliphatic aldehydes for the synthesis of α-amino nitriles.
Related Articles:
A convenient synthesis of N??Boc??protected α??aminonitriles from α??amidosulfones
[Banphavichit, Vorawit; Chaleawlertumpon, Saowaluk; Bhanthumnavin, Worawan; Vilaivan, Tirayut Synthetic Communications, 2004 , vol. 34, # 17 p. 3147 - 3160]
[Armstrong, Alan; Edmonds, Ian D.; Swarbrick, Martin E.; Treweeke, Nigel R. Tetrahedron, 2005 , vol. 61, # 35 p. 8423 - 8442]