ol7b00679_si_002.cif (433.84 kB)

Base-Controlled Diastereoselective Synthesis of Either anti- or syn-β-Aminonitriles

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posted on 20.03.2017, 21:50 by James C. Anderson, Ian B. Campbell, Sebastien Campos, Christopher D. Rundell, Jonathan Shannon, Graham J. Tizzard
Deprotonation of secondary alkane nitriles with nBuLi and addition to aryl imines gives kinetic anti-β-aminonitriles. Use of LHMDS allows reversible protonation of the reaction intermediate to give syn-β-aminonitriles. The pure diastereosiomers can be isolated in good yields, and the mechanism was elucidated.

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