Issue 6, 2021

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

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.

Graphical abstract: 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

Supplementary files

Article information

Article type
Research Article
Submitted
01 Dec 2020
Accepted
18 Jan 2021
First published
20 Jan 2021

Org. Chem. Front., 2021,8, 1243-1248

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

F. Li, S. Liang, Y. Luan, X. Chen, H. Zhao, A. Huang, P. Li and W. Li, Org. Chem. Front., 2021, 8, 1243 DOI: 10.1039/D0QO01505A

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