Synthesis of methanesulfone-containing tetrasubstituted carbon stereocenters

A methanesulfonylation reaction for the synthesis of sulfone-containing tetrasubstituted carbon stereocenters is described for the first time by simple treatment of indanedione-chromanone synthons with Et 3 N and easily accessible MsCl without any use of organometallic chemistry. This technology gav...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2021-03, Vol.19 (1), p.2269-2276
Main Authors: Zhou, Wei, Tian, You-Ping, Zhou, Hao-Jie, Wang, Hui-Juan, Ren, Yan, Liu, Xiong-Li
Format: Article
Language:English
Subjects:
Carbon
Chemical synthesis
Crystallography
Organometallic compounds
Single crystals
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Summary:A methanesulfonylation reaction for the synthesis of sulfone-containing tetrasubstituted carbon stereocenters is described for the first time by simple treatment of indanedione-chromanone synthons with Et 3 N and easily accessible MsCl without any use of organometallic chemistry. This technology gave the corresponding valuable chromone-based 2-methanesulfonylated 1,3-indanediones in good yields (up to 89% yield) under mild conditions. The present work provides an attractive strategy for the construction of biologically interesting sulfone-containing tetrasubstituted carbon stereocenters, which might be valuable in medicinal chemistry. Synthesis of sulfone-containing tetrasubstituted carbon stereocenters.
ISSN:1477-0520
1477-0539
DOI:10.1039/d1ob00071c