Tetrahedron

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

文献索引：Kadam, Santosh T.; Thirupathi, Ponnaboina; Kim, Sung Soo Tetrahedron, 2010 , vol. 66, # 9 p. 1684 - 1688

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被引用次数: 8

摘要

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.