Enantioselective Copper-Catalyzed Borylative Amidation of Allenes

Autor:	Seunghwan Byun, Abdikani Omar Farah, Henry R. Wise, Andrew Katchmar, Paul H.-Y. Cheong, Karl A. Scheidt
Rok vydání:	2022
Předmět:	Acrylamide Colloid and Surface Chemistry Molecular Structure Stereoisomerism General Chemistry Amides Biochemistry Copper Catalysis
Zdroj:	Journal of the American Chemical Society. 144:22850-22857
ISSN:	1520-5126 0002-7863
Popis:	An approach for the copper-catalyzed synthesis of enantioenriched amides bearing an α-stereogenic center is disclosed. This method involves the addition of an allyl copper species to an isocyanate and allows access to α-substituted chiral amides in high yields and high-to-excellent enantioselectivities. The utility of α-vinyl β-boryl amides in synthesis is highlighted by the diversification of products to afford highly useful scaffolds. DFT calculations reveal that the catalyst preferentially coordinates to the oxygen of the isocyanate. Enantiocontrol arises from the steric repulsion between the boryl group and the stereodirecting phenyl of the chiral ligand.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::30dc89aa50eef7039df745944ee3e270 https://doi.org/10.1021/jacs.2c10507 Zobrazit plný text záznamu