Carbene‐Catalyzed Direct Functionalization of the β‐sp3‐Carbon Atoms of α‐Chloroaldehydes. Issue 55 (10th September 2019)

• Record Type: Journal Article
• Authors: Liu, Bin; Luo, Guoyong; Wang, Hongling; Hao, Lin; Yang, Song; Jin, Zhichao; Chi, Yonggui Robin
• Is Part Of: Chemistry. Volume 25:Issue 55(2019)
• Page Start: 12719
• Page End: 12723
• Publication Date: 2019-09-10
• Subjects: carbene catalysis -- α-chloroaldehydes -- homoenolates -- NHC; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201903592
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: A direct functionalization of the β‐sp 3 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‐sp 3 ‐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. Abstract : Inert carbon activation : Direct functionalization of the β‐sp 3 carbon atoms of α‐chloro aldehydes under the influence of a N‐heterocyclic carbene (NHC) organic catalyst is realized (see scheme).