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Directed lithiation on the quinuclidine ring system: the synthesis of 2,3-difunctionalised quinuclidines
Authors:Ian A. O&rsquo  Neil,James Hitchin,Alan P. Chorlton
Affiliation:a Robert Robinson Laboratories, Department of Chemistry, University of Liverpool, Crown Street, Liverpool L69 7ZD, UK
b Pharmorphix Ltd, 250 Milton Science Park, Cambridge CB4 0WE, UK
Abstract:
Lithiation of 3-methoxymethyl quinuclidine N-oxide occurs regioselectively to generate the 2-lithio 3-methoxymethyl derivative which can be trapped out with non-enolisable electrophiles to give 2,3-disubstituted quinuclidine N-oxide derivatives in good yield.
Keywords:Amine oxide   Lithiation   Quinuclidine
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