Catalytic enantioselective reaction. Part 9. 1,2-O-Isopropylidene-5-deoxy-5-N,N-dialkyl (or -N-monoalkyl)amino-α-D-xylofuranose derivatives as highly effective chiral catalysts for enantioselective addition of diethylzinc to aliphatic and aromatic aldehydes
- 1 January 1996
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 24,p. 2901-2907
- https://doi.org/10.1039/p19960002901
Abstract
A series of new 1,2-O-isopropylidene-5-deoxy-5-N,N-dialkyl (or-N-monoalkyl)amino-α-D-xylofuranose derivatives have been prepared form D-xylose and their enantioselectivities as chiral catalysts for the addition of diethylzinc to aldehydes have been examined. Or the chiral catalysts examined, 5-deoxy-1,2-O-isopropylidene-5-morpholino-α-D-xylofuranose provides high enantioselectivity for aromatic and relatively hindered aliphatic aldehydes, and 5-deoxy-5-hexaydroazepinyl-1,2-O-isopropylidene-α-D-xylofuranose is highly effective for unhindered aliphatic aldehydes.Keywords
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