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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.
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2010 (English)In: Tetrahedron: asymmetry, ISSN 0957-4166, E-ISSN 1362-511X, Vol. 21, no 11-12, p. 1374-1381Article in journal (Refereed) Published
Abstract [en]

4-Substituted bicyclo[2.2.2]octane-2,6-diones I [R = acetyl, benzyl, allyl, etc.] have been synthesized and tested as substrates in the enantioselective redn. with baker's yeast to give the corresponding hydroxy ketones II [R = acetyl, benzyl, allyl, etc.]. It was found that the deriv. 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 derivs. were reduced with varying yields (36-87%) and ees (10-82%). The best result was obtained for the 4-Oallyl deriv. (80% yield, 82% ee). The hydroxy ketones carrying the benzyloxy and allyloxy groups at the 4-position were converted into the corresponding BODOLs III [R = allyl, benzyl], which were tested as catalysts in the diethylzinc addn. to benzaldehyde. In this reaction the ees were 90% and 89%, resp., which showed that BODOLs substituted at the 4-position are essentially as good catalysts in this reaction as those bearing a hydrogen. [on SciFinder(R)]

Place, publisher, year, edition, pages
Elsevier Ltd. , 2010. Vol. 21, no 11-12, p. 1374-1381
Keywords [en]
bridgehead substituted bicyclooctanedione baker yeast redn, bicyclooctane hydroxy ketone prepn, BODOL prepn diethylzinc addn benzaldehyde
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-374754DOI: 10.1016/j.tetasy.2010.06.003OAI: oai:DiVA.org:uu-374754DiVA, id: diva2:1282028
Note

Copyright (C) 2019 American Chemical Society (ACS). All Rights Reserved.; CAPLUS AN 2010:964417(Journal)

Available from: 2019-01-23 Created: 2019-01-23 Last updated: 2019-01-23

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Larsson, Johanna M.
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