4-Hydroxyphenylglycine-Based Polymer-Bound Amino Alcohols and insitu- Generated Oxazaborolidines for Enantioselective Reductions

Author(s): Manfred Braun, Michael Sigloch, Jens Cremer.

Journal Name: Letters in Organic Chemistry

Volume 5 , Issue 4 , 2008

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Abstract:

The chiral amino alcohol HOC6H4CH(NH2)C(C6H5)2OH (4) that is derived from (R)-4-hydroxyphenylglycine has been converted into novel soluble and insoluble polymer-bound reagents 5. After in-situ conversion into oxazaborolidines, they serve for enantioselective reductions of acetophenone to deliver (S)-1-phenylethanol (6) in up to 83% enantiomeric excess.

Keywords: Asymmetric synthesis, polystyrene, boron, ketone, catalysis

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Article Details

VOLUME: 5
ISSUE: 4
Year: 2008
Page: [244 - 248]
Pages: 5
DOI: 10.2174/157017808784049551
Price: $58