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Nucleophilic β-Carbon Activation of Propionic Acid as a 3-Carbon Synthon by Carbene Organocatalysis.

Chemistry (Weinheim an der Bergstrasse, Germany) (2015-05-28)
Zhichao Jin, Ke Jiang, Zhenqian Fu, Jaume Torres, Pengcheng Zheng, Song Yang, Bao-An Song, Yonggui Robin Chi
ABSTRACT

Direct β-carbon activation of propionic acid (C2H5CO2H) by carbene organocatalysis has been developed. This activation affords the smallest azolium homoenolate intermediate (without any substituent) as a 3-carbon nucleophile for enantioselective reactions. Propionic acid is an excellent raw material because it is cheap, stable, and safe. This approach provides a much better solution to azolium homoenolate synthesis than the previously established use of acrolein (enal without any substituent), which is expensive, unstable, and toxic.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Propionic acid, puriss. p.a., ≥99.5% (GC)