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