Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 48, Pages 15877-15881Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201810599
Keywords
aldol reaction; carboxylic acids; hypervalent silicon; organocatalysis; phosphine oxides
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Funding
- JSPS KAKENHI [16K08168]
- Ministry of Education, Culture, Sports, Science and Technology, Japan
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The first catalytic enantioselective aldol reaction of various unprotected carboxylic acids is described. In the presence of a chiral bis(phosphine oxide) as a Lewis base catalyst, carboxylic acids were activated with silicon tetrachloride to form the corresponding bis(trichlorosilyl)enediolates in situ, which subsequently underwent an aldol reaction with an aldehyde or a ketone to produce beta-hydroxycarboxylic acids in high enantioseledivities of up to 92% ee.
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