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From (Phenylsulfanyl)cycloalkanecarbaldehydes to Optically Active Spirocyclic Tetrahydrofurans: Stereospecific Resolution of Symmetric Aldehydes through ( S )‐Proline‐Catalysed Aldol Reaction
Author(s) -
Secci Francesco,
Frongia Angelo,
Rubanu Maria Grazia,
Sechi Maria Laura,
Sarais Giorgia,
Arca Massimiliano,
Piras Pier Paolo
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402653
Subject(s) - stereospecificity , aldol reaction , chemistry , enantioselective synthesis , ketone , tetrahydrofuran , stereochemistry , proline , optically active , organic chemistry , catalysis , amino acid , biochemistry , solvent
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)cycloalkanecarbaldehydes followed by a ketone reduction, acid‐catalysed [1,2]‐SPh stereospecific migration, and ring‐closure reaction.