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Carbene-Catalyzed Direct Functionalization of the β-sp3 -Carbon Atoms of α-Chloroaldehydes
Bin Liu1,2, Guoyong Luo3,2, Hongling Wang1
1Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang, 550025, P. R. China.
Abstract:
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.
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