期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 140, 期 35, 页码 11067-11075出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.8b05819
关键词
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资金
- Spanish Ministerio de Ciencia e Innovation [CTQ2016-76908-C2-1-P, CTQ2016-76908-C2-2-P, CTQ2016-78083-P, RYC-2013-12585]
- Junta de Andalucia [2012/FQM 10787]
- European Union's Seventh Framework Program, Marie Sklodowska-Curie actions for a Talent Hub fellowship (COFUND) [291780]
- University of Seville [1800511201]
A highly diastereo- and enantioselective, scalable Pd-catalyzed dynamic kinetic asymmetric Heck reaction of heterobiaryl sulfonates with electron-rich olefins is described. The coupling of 2,3-dihydrofuran or N-boc protected 2,3-dihydropyrrole with a variety of quinoline, quinazoline, phthalazine, and picoline derivatives takes place with simultaneous installation of central and axial chirality, reaching excellent diastereo- and enantiomeric excesses when in situ formed [Pd-0/DM-BINAP] was used as the catalyst, with loadings reduced down to 2 mol % in large scale reactions. The coupling of acyclic, electron-rich alkenes can also be performed using a [Pd-0/Josiphos ligand] to obtain axially chiral heterobiaryl alpha-substituted alkenes in high yields and enantioselectivities. Products from Boc-protected 2,3-dihydropyrrole can be easily transformed into N,N ligands or appealing axially chiral, bifunctional proline-type organocatalysts. Computational studies suggest that a beta-hydride elimination is the stereocontrolling step, in agreement with the observed stereochemical outcome of the reaction.
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