A synthetic and spectroscopic investigation of the asymmetric α-lithiation-trapping of six-membered N-Boc heterocycles using Alexakis diamines

James Firth, Giacomo Gelardi, Peter John Rayner, Darren Stead, Peter Andrew O'Brien

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The asymmetric lithiation-trapping of six-membered N-Boc heterocycles using s-BuLi and two different Alexakis diamines is reported. These readily available ligands outperform the current ‘best-in-class’ sparteine-type diamines in the lithiation and benzophenone trapping of N-Boc piperazines and the lithiation-cyclisation-trapping of N-Boc-4-chloropiperidine. In situ IR spectroscopy has been used to optimise lithiation times and to discover previously unknown subtleties regarding the lithiation step.
Original languageEnglish
Pages (from-to)1288-1303
Issue number2
Publication statusPublished - 20 Jun 2018

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