Boron-Catalyzed Carboxylic Acid-Selective Aldol Reaction with Trifluoromethyl Ketones

A catalytic carboxylic acid-selective aldol reaction with trifluoromethyl ketones was developed. Reversible and selective covalent bond formation between a boron catalyst and a carboxylic acid is key to realizing the unprecedented catalytic aldol reaction of simple carboxylic acids. The reaction pro...

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Bibliographic Details
Published inChemical & pharmaceutical bulletin Vol. 66; no. 3; pp. 231 - 234
Main Authors Ishizawa, Kouhei, Nagai, Hideoki, Shimizu, Yohei, Kanai, Motomu
Format Journal Article
LanguageEnglish
Published Japan The Pharmaceutical Society of Japan 01.03.2018
Japan Science and Technology Agency
Subjects
Acids
Aldehydes
aldol reaction
Boron
boron catalyst
carboxylic acid
Carboxylic acids
Catalysis
Covalent bonds
Functional groups
Indomethacin
Ketones
Substrates
trifluoromethyl ketone
boron catalyst
aldol reaction
carboxylic acid
trifluoromethyl ketone
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Summary:A catalytic carboxylic acid-selective aldol reaction with trifluoromethyl ketones was developed. Reversible and selective covalent bond formation between a boron catalyst and a carboxylic acid is key to realizing the unprecedented catalytic aldol reaction of simple carboxylic acids. The reaction proceeded chemoselectively at the α-position of carboxylic acid even in the presence of ketone, ester, or amide functional groups in the donor substrates. The chemoselectivity is beneficial for late-stage derivatizations of biologically relevant compounds, as demonstrated by the conversion of indomethacin and triacetylcholic acid.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.c17-00545