Thiophenol-mediated 1,5-hydrogen transfer for the preparation of pyrrolizidines, indolizidines, and related compounds

Authors :: Fabrice Dénès
Philippe Renaud
Florent Beaufils
Chimie Et Interdisciplinarité : Synthèse, Analyse, Modélisation (CEISAM)
Université de Nantes - UFR des Sciences et des Techniques (UN UFR ST)
Université de Nantes (UN)-Université de Nantes (UN)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)
Source :: Organic Letters, Organic Letters, American Chemical Society, 2007, 9 (21), pp.4375-4378
Publication Year :: 2007
Abstract: The efficient preparation of 1-azabicyclic alkanes is described. Highly functionalized skeletons are prepared in a concise manner using a radical tin-free 1,5-hydrogen transfer−cyclization process. The precursors for the radical reactions are readily assembled either from pyrrolidine/piperidine/hexahydro-1H-azepine or via condensation of a properly designed N-alkylimine with an allenylzinc species.

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