Asymmetric baker's yeast reductions of bridgehead-substituted bicyclo[2.2.2]octane-2,6-dione derivatives followed by conversion into catalytically active BODOLs for the diethylzinc addition to benzaldehyde
(2010) In Tetrahedron: Asymmetry 21(11-12). p.1374-1381- Abstract
- 4-Substituted bicyclo[2.2.2]octane-2,6-diones have been synthesized and tested as substrates in the enantioselective reduction with baker's yeast to give the corresponding hydroxy ketones. It was found that the derivative bearing a TIPSO group at the 4-position was not reduced at all while that with a TBDMSO group gave 87% yield and 46% ee. Other 4-oxy functionalized derivatives were reduced with varying yields (36-87%) and ees (10-82%). The best result was obtained for the 4-Oallyl derivative (80% yield, 82% ee). The hydroxy ketones carrying the benzyloxy and allyloxy groups at the 4-position were converted into the corresponding BODOLs, which were tested as catalysts in the diethylzinc addition to benzaldehyde. In this reaction the ees... (More)
- 4-Substituted bicyclo[2.2.2]octane-2,6-diones have been synthesized and tested as substrates in the enantioselective reduction with baker's yeast to give the corresponding hydroxy ketones. It was found that the derivative bearing a TIPSO group at the 4-position was not reduced at all while that with a TBDMSO group gave 87% yield and 46% ee. Other 4-oxy functionalized derivatives were reduced with varying yields (36-87%) and ees (10-82%). The best result was obtained for the 4-Oallyl derivative (80% yield, 82% ee). The hydroxy ketones carrying the benzyloxy and allyloxy groups at the 4-position were converted into the corresponding BODOLs, which were tested as catalysts in the diethylzinc addition to benzaldehyde. In this reaction the ees were 90% and 89%, respectively, which showed that BODOLs substituted at the 4-position are essentially as good catalysts in this reaction as those bearing a hydrogen. (C) 2010 Elsevier Ltd. All rights reserved. (Less)
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- author
- Manner, Sophie LU ; Hansson, Cecilia ; Larsson, Johanna ; Oltner, Viveca and Frejd, Torbjörn LU
- organization
- publishing date
- 2010
- type
- Contribution to journal
- publication status
- published
- subject
- in
- Tetrahedron: Asymmetry
- volume
- 21
- issue
- 11-12
- pages
- 1374 - 1381
- publisher
- Elsevier
- external identifiers
-
- wos:000281095300009
- scopus:77956647429
- ISSN
- 0957-4166
- DOI
- 10.1016/j.tetasy.2010.06.003
- 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
- 221fcbdf-d0f1-4c43-acd8-0a668ecaa9f1 (old id 1673548)
- date added to LUP
- 2016-04-01 14:59:15
- date last changed
- 2022-01-28 03:26:40
@article{221fcbdf-d0f1-4c43-acd8-0a668ecaa9f1, abstract = {{4-Substituted bicyclo[2.2.2]octane-2,6-diones have been synthesized and tested as substrates in the enantioselective reduction with baker's yeast to give the corresponding hydroxy ketones. It was found that the derivative bearing a TIPSO group at the 4-position was not reduced at all while that with a TBDMSO group gave 87% yield and 46% ee. Other 4-oxy functionalized derivatives were reduced with varying yields (36-87%) and ees (10-82%). The best result was obtained for the 4-Oallyl derivative (80% yield, 82% ee). The hydroxy ketones carrying the benzyloxy and allyloxy groups at the 4-position were converted into the corresponding BODOLs, which were tested as catalysts in the diethylzinc addition to benzaldehyde. In this reaction the ees were 90% and 89%, respectively, which showed that BODOLs substituted at the 4-position are essentially as good catalysts in this reaction as those bearing a hydrogen. (C) 2010 Elsevier Ltd. All rights reserved.}}, author = {{Manner, Sophie and Hansson, Cecilia and Larsson, Johanna and Oltner, Viveca and Frejd, Torbjörn}}, issn = {{0957-4166}}, language = {{eng}}, number = {{11-12}}, pages = {{1374--1381}}, publisher = {{Elsevier}}, series = {{Tetrahedron: Asymmetry}}, title = {{Asymmetric baker's yeast reductions of bridgehead-substituted bicyclo[2.2.2]octane-2,6-dione derivatives followed by conversion into catalytically active BODOLs for the diethylzinc addition to benzaldehyde}}, url = {{http://dx.doi.org/10.1016/j.tetasy.2010.06.003}}, doi = {{10.1016/j.tetasy.2010.06.003}}, volume = {{21}}, year = {{2010}}, }