Herein, we report
a nickel-catalyzed reductive cross-coupling reaction
of easily accessible 3-butenyl carbamoyl chloride with primary alkyl
iodide to access the chiral α-alkylated pyrrolidinone
with broad substrate scope and high enantiomeric excess. The
current art of synthesis still remains challenging on the enantioselective
α-monoalkylation of pyrrolidinones. The newly designed
chiral 8-quinoline imidazoline ligand (Quinim) is crucial for maintaining
the reactivity and enantioselectivity to ensure the reductive
cyclization of monosubstituted alkenes for unprecedented synthesis
of chiral non-aromatic heterocycles.
The development of carbamoyl chlorides as synthons for various amide-containing molecules and heterocycles have been summarized and discussed in this review article. Carbamoyl chlorides can participate in a diverse range...
Reported herein is a palladium/copper
cooperative-catalyzed dicarbofunctionalization of alkene-tethered
carbamoyl chlorides with 1,1-diborylmethane. This cyclization/deborylation
cascade strategy allows for the expedient formation of the versatile
borylated 3,3-disubstituted oxindole skeleton, allowing for further
functionalization via the derivatization of the carbon–boron
bond.
The construction of multi-stereocenters by a transition metal-catalyzed cross-coupling reaction is a major challenge. The catalytic desymmetric functionalization of unactivated alkenes remains largely unexplored. Herein, we disclose -a desymmetric dicarbofunctionalization of 1,6-dienes via a nickel-catalyzed reductive cross-coupling reaction. The leverage of the underdeveloped chiral 8-Quinox enables the Ni-catalyzed desymmetric carbamoylalkylation of both unactivated mono-and disubstituted alkenes to form pyrrolidinone bearing two nonadjacent stereogenic centers in high enantio-and stereoselectivitives with broad functional-group tolerance. The synthetic application of pyrrolidinones allows the rapid access to complex chiral fused-heterocycles.
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