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

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...

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Bibliographic Details
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
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Online Access:https://hdl.handle.net/10356/137756
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Institution: Nanyang Technological University
Language: English
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Summary: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.