Journal
CHIRALITY
Volume 25, Issue 10, Pages 643-647Publisher
WILEY
DOI: 10.1002/chir.22190
Keywords
aldol reaction; Lewis bases; organocatalysis; stereoselectivity; tetrachlorosilane
Funding
- MIUR
- European COST Action [CM0905]
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The direct aldol reaction between aryl methyl ketones with aromatic aldehydes in the presence of tetrachlorosilane and a catalytic amount of a chiral bithiophene diphosphine oxide was studied; the product of double aldol addition was isolated as diacetate in good diastereoselectivity (up to 95:5) and enantioselectivities up to 91%. The reaction with heteroaromatic aldehydes was also investigated leading to the corresponding 1,3 diols, in some cases with excellent stereoselectivities. Chirality 25:643-647:, 2013. (c) 2013 Wiley Periodicals, Inc.
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