Novel, cyclic and bicyclic 1,3-diols as catalysts for the diethylzinc addition to aldehydes
(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.
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/342790
- author
- Sarvary, Ian LU ; Wan, YQ and Frejd, Torbjörn LU
- organization
- publishing date
- 2002
- 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}}, }