Organocatalytic regio-, diastereo- and enantioselective γ-additions of isoxazol-5(4H)-ones to β,γ-alkynyl-α-imino esters for the synthesis of axially chiral tetrasubstituted α-amino allenoates
Literature Information
Publication Date
2021-01-20
DOI
10.1039/D0QO01505A
Impact Factor
5.281
Authors
Fushuai Li, Shuai Liang, Yepeng Luan, Xuling Chen, Hanhui Zhao, Anqi Huang, Pengfei Li, Wenjun Li
View Original
Abstract
The chiral phosphoric acid catalyzed regio-, diastereo- and enantioselective reaction of isoxazol-5(4H)-ones with β,γ-alkynyl-α-imino esters has been developed. With the established methodology, γ-addition of β,γ-alkynyl-α-imino esters and C-allenylation of isoxazol-5(4H)-ones were achieved with high regio- and stereoselectivities, affording diverse α-imino allenoates featuring an adjacent quaternary carbon stereocenter and an axially chiral tetrasubstituted allene motif in high yields.
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Organic Chemistry Frontiers
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