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

Sarvary, Ian LU ; Wan, YQ and Frejd, Torbjörn LU (2002) In Perkin Transactions 1 p.645-651
Abstract
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.
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Perkin Transactions 1
issue
5
pages
645 - 651
publisher
Royal Society of Chemistry
external identifiers
  • wos:000174032100012
  • scopus:0036006418
ISSN
1472-7781
DOI
10.1039/b110082n
language
English
LU publication?
yes
id
ed52aa69-d3f9-46d2-838d-aeda6fcacf73 (old id 342790)
date added to LUP
2007-11-12 15:44:22
date last changed
2017-08-27 05:31:07
@article{ed52aa69-d3f9-46d2-838d-aeda6fcacf73,
  abstract     = {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.},
  author       = {Sarvary, Ian and Wan, YQ and Frejd, Torbjörn},
  issn         = {1472-7781},
  language     = {eng},
  number       = {5},
  pages        = {645--651},
  publisher    = {Royal Society of Chemistry},
  series       = {Perkin Transactions 1},
  title        = {Novel, cyclic and bicyclic 1,3-diols as catalysts for the diethylzinc addition to aldehydes},
  url          = {http://dx.doi.org/10.1039/b110082n},
  year         = {2002},
}