Kinetic Resolution of Allyltriflamides through a Pd-Catalyzed C–H Functionalization with Allenes: Asymmetric Assembly of Tetrahydropyridines
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American Chemical Society
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Abstract
Enantioenriched, six-membered azacycles are essential structural motifs in many products of pharmaceutical or agrochemical interest. Here we report a simple and practical method for enantioselective assembly of tetrahydropyridines, which is paired to a kinetic resolution of α-branched allyltriflamides. The reaction consists of a formal (4+2) cycloaddition between the allylamine derivatives and allenes and is initiated by a palladium(II)-catalyzed C–H activation process. Both the chiral allylamide precursors and the tetrahydropyridine adducts were successfully obtained in high yields, with excellent enantioselectivity (up to 99% ee) and selectivity values of up to 127
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J. Am. Chem. Soc. 2021, 143, 10, 3747–3752
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https://doi.org/10.1021/jacs.1c01929Sponsors
This work has received financial support from Spanish grants (SAF2016-76689-R, CTQ2016-77047-P, PID2019-108624RBI00, PID2019-110385GB-I00, and FPI fellowship to B.C.), the
Consellería de Cultura, Educación e Ordenación Universitaria (ED431C 2017/19, 2015-CP082 and Centro Singular de Investigación de Galicia accreditation 2019-2022, ED431G 2019/03 and J. M. G fellowship), the European Regional Development Fund (ERDF), and the European Research Council (Advanced Grant No. 340055). The orfeo-cinqa network CTQ2016-81797-REDC is also kindly acknowledged
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© 2021 American Chemical Society. This is an open access article under the CC Attribution 4.0 International (CC BY 4.0) license (http://creativecommons.org/licenses/by/4.0/)