An enantioselective radical alkylation
of 4-alkyl-1,4-dihydropyridines
with Morita–Baylis–Hillman (MBH) adducts has been reported.
The SN2-type products are predominant. This reaction is
enabled by dual photoredox/palladium catalysis. The alkylation products
are provided in good yields with good regio- and enantioselectivity.
The use of Ding’s spiroketal-based bis(phosphine) (SKP) ligand
is crucial to achieving satisfactory regio- and enantioselectivity.
The resultant α,β-unsaturated ester can be easily reduced
to a synthetically useful chiral allyl alcohol.
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