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Novel, cyclic and bicyclic 1,3-diols as catalysts for the diethylzinc addition to aldehydes

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Author

Summary, in English

A number of optically pure 1,3-diols have been synthesized and used as catalysts in the asymmetric addition of diethylzinc to aromatic aldehydes. Enantiomeric excesses of up to 92% of (R)-1-phenylpropan-1-ol were obtained with anisylbicyclo[2.2.2] octanediol (14) as a catalyst. Using 2-picolylbicyclo[ 2.2.2] ocatanediol (16) as the catalyst resulted in a reversal of the stereoselectivity, yielding (S)-1-phenylpropan-1-ol in 83% ee. A pronounced positive non-linear effect was observed when varying the enantiomeric purity of catalyst 14.

Publishing year

2002

Language

English

Pages

645-651

Publication/Series

Journal of the Chemical Society - Perkin Transactions 1

Issue

5

Document type

Journal article

Publisher

Royal Society of Chemistry

Topic

  • Organic Chemistry

Status

Published

ISBN/ISSN/Other

  • ISSN: 1472-7781