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Synlett 1996; 1996(8): 731-733
DOI: 10.1055/s-1996-5518
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Enantioselective Synthesis of Protected α-Hydroxy Aldehydes and Related 1,2-Amino Alcohols. Applications to the Synthesis of (-)-exo- and (-)-endo-Brevicomin

Stephan Vettel, Christian Lutz, Paul Knochel*
  • *Fachbereich Chemie der Philipps-Universität Marburg, Hans-Meerwein-Str., D-35032 Marburg, Germany, Knochel@ps1515.chemi.uni-marburg.de
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Publikationsdatum:
31. Dezember 2000 (online)

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Chiral allylic alcohols which were prepared by the addition of functionalized dialkylzincs to α,β-unsaturated aldehydes in good to excellent enantioselectivity, were converted to protected α-hydroxy aldehydes and 1,2-amino alcohols without loss of optical purity. A functionalized α-silyloxy aldehyde prepared in this way was converted to optically pure (-)-exo- and (-)-endo-brevicomin (> 99 % ee).

Asymmetric catalysis - diorganozincs - chiral α-hydroxy aldehydes - 1,2-amino alcohols - (-)-exo-/(-)-endo-brevicomin