%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