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Nucleophilic β‐Carbon Activation of Propionic Acid as a 3‐Carbon Synthon by Carbene Organocatalysis
Author(s) -
Jin Zhichao,
Jiang Ke,
Fu Zhenqian,
Torres Jaume,
Zheng Pengcheng,
Yang Song,
Song BaoAn,
Chi Yonggui Robin
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201501481
Subject(s) - nucleophile , synthon , carbene , organocatalysis , substituent , enantioselective synthesis , chemistry , carbon fibers , organic chemistry , combinatorial chemistry , catalysis , materials science , composite number , composite material
Direct β‐carbon activation of propionic acid (C 2 H 5 CO 2 H) 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.