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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 Journal of the Chemical Society - 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
; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Journal of the Chemical Society - 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
additional info
The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)
id
ed52aa69-d3f9-46d2-838d-aeda6fcacf73 (old id 342790)
date added to LUP
2016-04-01 16:39:13
date last changed
2023-04-03 16:03:30
@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       = {{Journal of the Chemical Society - 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}},
  doi          = {{10.1039/b110082n}},
  year         = {{2002}},
}