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

Manfred      Braun; Michael      Sigloch; Jens      Cremer

doi:10.2174/157017808784049551

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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Letters in Organic Chemistry

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

Volume: 5 Issue: 4

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

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

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.

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Braun Manfred, Sigloch Michael and Cremer Jens, 4-Hydroxyphenylglycine-Based Polymer-Bound Amino Alcohols and insitu- Generated Oxazaborolidines for Enantioselective Reductions, Letters in Organic Chemistry 2008; 5 (4) . https://dx.doi.org/10.2174/157017808784049551