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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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author
organization
publishing date
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
id
221fcbdf-d0f1-4c43-acd8-0a668ecaa9f1 (old id 1673548)
date added to LUP
2010-09-23 09:36:17
date last changed
2018-05-29 11:47:26
@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},
  volume       = {21},
  year         = {2010},
}