Rh-Catalyzed Highly Enantioselective Synthesis of Aliphatic Sulfonyl Fluorides

Rh-catalyzed, highly enantioselective (up to 99.8% ee) synthesis of aliphatic sulfonyl fluorides was accomplished. This protocol provides a portal to a class of novel 2-aryl substituted chiral sulfonyl fluorides, which are otherwise extremely difficult to access. This asymmetric synthesis has the fe...

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Bibliographic Details
Published in:iScience 2019-11, Vol.21, p.695-705
Main Authors: Moku, Balakrishna, Fang, Wan-Yin, Leng, Jing, Li, Linxian, Zha, Gao-Feng, Rakesh, K.P., Qin, Hua-Li
Format: Article
Language:English
Subjects:
Catalysis
Organic Chemistry
Stereochemistry
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Summary:Rh-catalyzed, highly enantioselective (up to 99.8% ee) synthesis of aliphatic sulfonyl fluorides was accomplished. This protocol provides a portal to a class of novel 2-aryl substituted chiral sulfonyl fluorides, which are otherwise extremely difficult to access. This asymmetric synthesis has the feature of mild conditions, excellent functional group compatibility, and wide substrate scope (51 examples) generating a wide array of structurally unique chiral β-arylated sulfonyl fluorides for sulfur(VI) fluoride exchange (SuFEx) click reaction and drug discovery. [Display omitted] •Enantioselective synthesis of di(hetero)arylalkyl sulfonyl fluorides were achieved•These novel SuFEx Clickable molecules will play significant roles for drug discovery•The asymmetric C-C bond construction is a new portal to chiral sulfonyl fluorides•This protocol feathers with mild condition, wide scope, and excellent compatibility Catalysis; Organic Chemistry; Stereochemistry
ISSN:2589-0042
2589-0042
DOI:10.1016/j.isci.2019.10.051