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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

Manner, Sophie LU ; Hansson, Cecilia ; Larsson, Johanna ; Oltner, Viveca and Frejd, Torbjörn LU (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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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
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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}},
}