Issue 31, 2023

Enantioselective [3+2]-cycloaddition of 2,3-disubstituted cyclobutenones: vicinal quaternary stereocenters construction and skeletal functionalization

Abstract

Cycloaddition is a fundamental transformation, featuring the assembly of complex cyclic molecules with multiple stereocenters. We report here a silver-catalyzed [3+2]-cycloaddition of 2,3-disubstituted cyclobutenones with an array of azomethine ylide precursors iminoesters, furnishing azabicycles in good yields and enantioselectivities. Up to three contiguous all-carbon quaternary centers, including two angular stereocenters, could be constructed efficiently, due to high reactivity of strained cyclobutenones. Subsequent skeletal remodeling provided versatile molecules with distinct structural characters.

Graphical abstract: Enantioselective [3+2]-cycloaddition of 2,3-disubstituted cyclobutenones: vicinal quaternary stereocenters construction and skeletal functionalization

Supplementary files

Article information

Article type
Edge Article
Submitted
16 May 2023
Accepted
13 Jul 2023
First published
15 Jul 2023
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2023,14, 8355-8359

Enantioselective [3+2]-cycloaddition of 2,3-disubstituted cyclobutenones: vicinal quaternary stereocenters construction and skeletal functionalization

L. Lu and P. Lu, Chem. Sci., 2023, 14, 8355 DOI: 10.1039/D3SC02485G

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