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.
Department of Chemistry, University College London , 20 Gordon Street, London WC1H 0AJ, U.K.
James C
0000-0001-8120-4125
JC
Anderson
Department of Chemistry, University College London , 20 Gordon Street, London WC1H 0AJ, U.K.
Ian B
IB
Campbell
Department of Chemistry, University College London , 20 Gordon Street, London WC1H 0AJ, U.K.
Sebastien
S
Campos
Department of Chemistry, University College London , 20 Gordon Street, London WC1H 0AJ, U.K.
Christopher D
CD
Rundell
Department of Chemistry, University College London , 20 Gordon Street, London WC1H 0AJ, U.K.
Jonathan
J
Shannon
Department of Chemistry, University College London , 20 Gordon Street, London WC1H 0AJ, U.K.
Graham J
GJ
Tizzard