期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 142, 期 37, 页码 15860-15869出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.0c05976
关键词
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资金
- National Natural Science Foundation of China [21871150]
- Fundamental Research Funds for Central University
- China Postdoctoral Science Foundation [2019M660973]
Chiral sulfones are important structural motifs in organic synthesis because of their widespread use in pharmaceutical chemistry. In particular, chiral allylic sulfones have drawn particular interest because of their synthetic utility. However, enantioselective synthesis of 1,3-disubstituted unsymmetrical chiral allylic sulfones remains a challenge. In this article, we report a protocol for (R)-DTBM-Segphos/Pd-catalyzed regio- and enantioselective hydrosulfonylation of 1,3-dienes with sulfinic acids, which provides atomand step-economical access to 1,3-disubstituted chiral allylic sulfones. The reaction occurs under mild conditions and has a broad substrate scope. Combined experimental and computational studies suggest that the reaction is initiated by a ligand-to-ligand hydrogen transfer followed by a C-S bond reductive elimination via a six-membered transition state. Steric repulsion between the olefinic C-H of the substrate and the tert-butyl group of (R)-DTBM-Segphos was found to be a key factor in the enantiocontrol.
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