Amine-Catalyzed Decarboxylative Aldol Reaction of β-Ketocarboxylic Acids with Trifluoropyruvates

Decarboxylative aldol reaction of aliphatic carboxylic acids is a useful method for C−C bond formation because carboxylic acids are an easily available class of compounds. In this study, we found that the decarboxylative aldol reaction of tertiary β-ketocarboxylic acids and triflu...

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Bibliographic Details
Main Authors: Ryouta Kawanishi, Shinya Hattori, Seiji Iwasa, Kazutaka Shibatomi
Format: Article
Language:English
Published: MDPI AG 2019-07-01
Series:Molecules
Subjects:
Online Access:https://www.mdpi.com/1420-3049/24/15/2773
Description
Summary:Decarboxylative aldol reaction of aliphatic carboxylic acids is a useful method for C−C bond formation because carboxylic acids are an easily available class of compounds. In this study, we found that the decarboxylative aldol reaction of tertiary β-ketocarboxylic acids and trifluoropyruvates proceeded smoothly to yield the corresponding aldol products in high yields and with high diastereoselectivity in the presence of a tertiary amine catalyst. In this reaction, we efficiently constructed a quaternary carbon center and an adjacent trifluoromethylated carbon center. This protocol was also extended to an enantioselective reaction with a chiral amine catalyst, and the desired product was obtained with up to 73% enantioselectivity.
ISSN:1420-3049