%0 Generic %A Anderson, James C. %A Campbell, Ian B. %A Campos, Sebastien %A Rundell, Christopher D. %A Shannon, Jonathan %A Tizzard, Graham J. %D 2017 %T Base-Controlled Diastereoselective Synthesis of Either anti- or syn-β-Aminonitriles %U https://acs.figshare.com/articles/dataset/Base-Controlled_Diastereoselective_Synthesis_of_Either_i_anti_i_-_or_i_syn_i_-_-Aminonitriles/4768219 %R 10.1021/acs.orglett.7b00679.s002 %2 https://ndownloader.figshare.com/files/7830082 %K alkane nitriles %K aryl imines %K Base-Controlled Diastereoselective Synthesis %K syn -β- aminonitriles %K diastereosiomer %K LHMDS %K -β-aminonitrile %K mechanism %K nBuLi %K syn -β- Aminonitriles Deprotonation %K yield %X 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. %I ACS Publications