The First Highly Enantioselective Alkynylation of Chloral: A Practical and Efficient Pathway to Chiral Trichloromethyl Propargyl Alcohols

A new, inexpensive chiral amino alcohol‐based ligand, (1S,2S)‐2‐N,N‐dimethylamino‐1‐(4‐nitrophenyl)‐3‐(tert‐butyloxy)propan‐1‐ol, was developed for the asymmetric alkynylation of chloral in high yield with up to 98% ee. The resulting chiral adduct (S)‐1‐trichloromethyl‐3‐phenyl‐2‐propyn‐1‐ol was hyd...

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Veröffentlicht in:Advanced synthesis & catalysis 2004-05, Vol.346 (6), p.669-674
Hauptverfasser: Jiang, Biao, Si, Yu-Gui
Format: Artikel
Sprache:eng
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Zusammenfassung:A new, inexpensive chiral amino alcohol‐based ligand, (1S,2S)‐2‐N,N‐dimethylamino‐1‐(4‐nitrophenyl)‐3‐(tert‐butyloxy)propan‐1‐ol, was developed for the asymmetric alkynylation of chloral in high yield with up to 98% ee. The resulting chiral adduct (S)‐1‐trichloromethyl‐3‐phenyl‐2‐propyn‐1‐ol was hydrogenated over 10% Pd/C to give the useful intermediate chiral trichloromethyl carbinol in quantitative yield, which was efficiently transformed into the pharmaceutically important building blocks 2‐hydroxy‐4‐phenylbutanoate and homophenylalanine in high yield with excellent enantiomeric excess.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.200303237