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Synlett 1997; 1997(1): 115-116
DOI: 10.1055/s-1997-719
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Facile Synthesis of α-Amino Nitriles Using Lanthanide Triflate as a Lewis Acid Catalyst

Shû Kobayashi* , Haruro Ishitani, Masaharu Ueno
  • *Department of Applied Chemistry, Faculty of Science, Science University of Tokyo (SUT), Kagurazaka, Shinjuku-ku, Tokyo 162, Fax 3-3260-4726
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Publication Date:
22 March 2004 (online)

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In the presence of a catalytic amount of lanthanide triflate, imines react with cyanotrimethylsilane (TMSCN) to afford α-amino nitriles in excellent yields. Although some imines are difficult to prepare and purify, three-component reactions of aldehydes, amines, and TMSCN proceeded smoothly. Effects of water in these reactions and application to asymmetric synthesis are also discussed.

Strecker reaction - lanthanide triflate - α-amino nitrile - cyanation - three-component reaction