A variety of enantiomerically enriched tetrahydrofuran spirocyclic derivatives have been synthesised by a sequential enantioselective proline-induced stereospecific resolution through aldol reaction of (E/Z)-(phenylsulfanyl)cycloalkane-carbaldehydes followed by a ketone reduction, acid-catalysed [1,2]-SPh stereospecific migration, and ring-closure reaction.
From (phenylsulfanyl)cycloalkanecarbaldehydes to optically active spirocyclic tetrahydrofurans: stereospecific resolution of symmetric aldehydes through (S)-proline-catalysed aldol reaction
SECCI, FRANCESCO;FRONGIA, ANGELO;SARAIS, GIORGIA;ARCA, MASSIMILIANO;
2014-01-01
Abstract
A variety of enantiomerically enriched tetrahydrofuran spirocyclic derivatives have been synthesised by a sequential enantioselective proline-induced stereospecific resolution through aldol reaction of (E/Z)-(phenylsulfanyl)cycloalkane-carbaldehydes followed by a ketone reduction, acid-catalysed [1,2]-SPh stereospecific migration, and ring-closure reaction.
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