ENANTIOSELECTIVE SYNTHESIS OF PROTECTED ALPHA-HYDROXY ALDEHYDES AND RELATED 1,2-AMINO ALCOHOLS - APPLICATIONS TO THE SYNTHESIS OF (-)-EXO-BREVICOMIN AND (-)-ENDO-BREVICOMIN

Authors
VETTEL S LUTZ C KNOCHEL P
Citation
S. Vettel et al., ENANTIOSELECTIVE SYNTHESIS OF PROTECTED ALPHA-HYDROXY ALDEHYDES AND RELATED 1,2-AMINO ALCOHOLS - APPLICATIONS TO THE SYNTHESIS OF (-)-EXO-BREVICOMIN AND (-)-ENDO-BREVICOMIN, Synlett, (8), 1996, pp. 731
Citations number
33
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synlett → ACNP
ISSN journal
09365214
Issue
8
Year of publication
1996
Database
ISI
SICI code
0936-5214(1996):8<731:ESOPAA>2.0.ZU;2-9
Abstract
Chiral allylic alcohols which were prepared by the addition of functio nalized dialkylzincs to alpha,beta-unsaturated aldehydes in good to ex cellent enantioselectivity, were converted to protected alpha-hydroxy aldehydes and 1,2-amino alcohols without loss of optical purity. A fun ctionalized alpha-silyloxy aldehyde prepared in this way was converted to optically pure (-)-exo- and (-)-endo-brevicomin (>99% ee).