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


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. 
DOI: 10.1021/acs.orglett.7b00679

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