ol7b00679_si_001.pdf (6.14 MB)
Base-Controlled Diastereoselective Synthesis of Either anti- or syn-β-Aminonitriles
journal contribution
posted on 2017-03-20, 21:50 authored by James C. Anderson, Ian B. Campbell, Sebastien Campos, Christopher D. Rundell, Jonathan Shannon, Graham J. TizzardDeprotonation
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.