Nucleophilic β-carbon activation of propionic acid as a 3-carbon synthon by carbene organocatalysis

• Main Authors: Chi, Robin Yonggui, Jin, Zhichao, Jiang, Ke, Fu, Zhenqian, Torres, Jaume, Zheng, Pengcheng, Yang, Song, Song, Bao-An
• Other Authors: School of Biological Sciences
• Format: Article
• Language: English
• Published: 2015
• Subjects: DRNTU::Science::Chemistry::Organic chemistry
• Online Access: https://hdl.handle.net/10356/103784; http://hdl.handle.net/10220/25876
• Institution: Nanyang Technological University

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.