Carbene-catalyzed direct functionalization of the β-sp3 -carbon atoms of α-chloroaldehydes

• Main Authors: Liu, Bin, Luo, Guoyong, Wang, Hongling, Hao, Lin, Yang, Song, Jin, Zhichao, Chi, Robin Yonggui
• Other Authors: School of Physical and Mathematical Sciences
• Format: Article
• Language: English
• Published: 2020
• Subjects: Science::Chemistry::Organic chemistry; Carbene Catalysis; α-Chloroaldehydes
• Online Access: https://hdl.handle.net/10356/137756
• Institution: Nanyang Technological University

A direct functionalization of the β-sp3 carbon atom of α-chloro aldehyde has been developed. The reaction starts with the addition of a carbene catalyst to α-chloroaldehyde to eventually form the homoenolate intermediate. This overall redox-neutral process successfully converts the otherwise inert β-sp3 -carbon atom of the aldehyde substrate to a nucleophilic carbon atom for asymmetric reactions. This study constitutes the first success in activating α-chloroaldehydes to generate homoenolate intermediates by carbene organic catalysis and shall encourage further explorations in using organic catalysis for transforming inert chemical bonds.