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

James C Anderson; Ian B Campbell; Sebastien Campos; Christopher D Rundell; Jonathan Shannon; Graham J Tizzard

doi:10.1021/acs.orglett.7b00679

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

Org Lett. 2017 Apr 7;19(7):1918-1921. doi: 10.1021/acs.orglett.7b00679. Epub 2017 Mar 21.

Authors

James C Anderson¹, Ian B Campbell¹, Sebastien Campos¹, Christopher D Rundell¹, Jonathan Shannon¹, Graham J Tizzard¹

Affiliation

¹ Department of Chemistry, University College London , 20 Gordon Street, London WC1H 0AJ, U.K.

PMID: 28322059
DOI: 10.1021/acs.orglett.7b00679

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't