Rh-Catalyzed Addition of Arylboroxines to Cyclic N-(Isopropanesulfinyl)ketimines

Autor:	Jonathan A. Ellman, Andrew W. Buesking, Hyung Hoon Jung
Rok vydání:	2012
Předmět:	chemistry.chemical_compound chemistry Organic Chemistry Disulfide bond chemistry.chemical_element Organic chemistry Cyclohexanone Isopropyl Rhodium Catalysis
Zdroj:	The Journal of Organic Chemistry. 77:9593-9600
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo301634y
Popis:	Arylboroxines, which are easily accessed by drying commercially available arylboronic acids, are added to N-(isopropanesulfinyl)ketimines derived from cyclohexanone, N-Boc-piperidin-4-one, and tetrahydropyran-4-one in high yields and with excellent functional group compatibility via rhodium catalysis. These results contrast with additions to the corresponding ketimines incorporating the larger N-tert-butanesulfinyl group, which give considerably lower yields. Efficient two-step preparation of racemic isopropanesulfinamide from inexpensive isopropyl disulfide and recycling of the isopropanesulfinyl group from the addition products are also described.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::0f5e959bf0e41372ba1d42e789f0b0b6 https://doi.org/10.1021/jo301634y Zobrazit plný text záznamu