From (Phenylsulfanyl)cycloalkanecarbaldehydes to Optically Active Spirocyclic Tetrahydrofurans: Stereospecific Resolution of Symmetric Aldehydes through ( S )‐Proline‐Catalysed Aldol Reaction | Zendy

Secci Francesco | Zendy; Frongia Angelo | Zendy; Rubanu Maria Grazia | Zendy; Sechi Maria Laura | Zendy; Sarais Giorgia | Zendy; Arca Massimiliano | Zendy; Piras Pier Paolo | Zendy

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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.

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