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

Tizzard, Graham J.

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

Posted on 2017-03-20 - 21:50

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.

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

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

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