Base-Controlled Diastereoselective Synthesis of Either <i>anti</i>- or <i>syn</i>-β-Aminonitriles

Published on 2017-03-20T21:50:21Z (GMT) by
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 <i>syn</i>-β-aminonitriles. The pure diastereosiomers can be isolated in good yields, and the mechanism was elucidated.

Cite this collection

Anderson, James C.; Campbell, Ian B.; Campos, Sebastien; Rundell, Christopher D.; Shannon, Jonathan; Tizzard, Graham J. (2017): Base-Controlled Diastereoselective Synthesis of Either anti- or syn-β-Aminonitriles. ACS Publications.

https://doi.org/10.1021/acs.orglett.7b00679

Retrieved: 14 29, Mar 27, 2017 (GMT)