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Updated: Feb 12, 2026

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Asymmetric Construction of Remote Vicinal Quaternary and Tertiary Stereocenters via Direct Doubly Vinylogous Michael
Subhrajit Rout1, Harshit Joshi1, Vinod K Singh1,2
1Department of Chemistry , Indian Institute of Technology Kanpur , Kanpur 208 016 , UP , India.
Abstract:
An asymmetric direct doubly vinylogous Michael addition has been developed for the generation of sterically congested vicinal quaternary and tertiary stereocenters. This doubly vinylogous Michael addition of β,γ-unsaturated butenolides to 3-methyl-4-nitro-5-alkenyl isoxazoles, powered by a bifunctional squaramide, affords a broad range of densely functionalized enantioenriched γ,γ-disubstituted butenolides in high yields with excellent diastereo- and enantioselectivities in most cases. Moreover, the strategy highlights the first application of β,γ-unsaturated butenolides in an asymmetric 1,6-conjugate addition.
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