Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 37, Pages 20204-20209Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202105452
Keywords
cobalt; desymmetrization; pyridine synthesis; quaternary carbon; regioselectivity
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Funding
- Shanghai Jiao Tong University
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A Co-catalyzed enantioselective desymmetric [2+2+2] cycloaddition has been developed for the synthesis of pyridines with all-carbon quaternary carbon centers, with regio- and enantioselectivities controlled by the nature of terminal alkynes and substituents on the bisoxazolinephosphine ligands. Pyridines with 5-substituents can be obtained with high regioselectivity and up to 94% ee, while pyridines with 6-substituents can be formed with up to 99% ee using different alkynes and ligands.
A Co-catalyzed enantioselective desymmetric [2+2+2] cycloaddition for synthesis of pyridines with all-carbon quaternary carbon centers has been developed. The regio- and enantioselectivities are controlled by the inherent nature of terminal alkynes and the substituents on the bisoxazolinephosphine ligands. Pyridines with 5-substitutents could be obtained with >20:1 regioselectivity and up to 94 % ee when terminal alkyl, alkenyl or silyl alkynes and DTBM/Ph-based NPN* ligand L6 were used. Terminal aryl alkynes and Ph/Bn-based ligand L4 leads to formation of pyridines with 6-substitutents in up to 99 % ee.
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