title: Access to Cyclic Amino Boronates via Rhodium-Catalyzed Functionalization of Alkyl MIDA Boronates.
abstract: Herein, we describe the rhodium-catalyzed C-H amination reaction of 1,2-boryl sulfamate esters derived from amphoteric α-boryl aldehydes. Depending on the substitution pattern of the boryl sulfamate ester, a diverse range of five- or six-membered ring heterocycles are accessible using this transformation. The highly chemoselective nature of the C-H functionalization reaction preserves the alkyl boronate functional group, which enables the synthesis of B-C-N and B-C-C-N motifs that are present in a number of hydrolase inhibitors.
authors.affiliation: Davenport Research Laboratories, Department of Chemistry, University of Toronto , 80 St. George Street, Toronto, ON, M5S 3H6, Canada.
authors.forename: Jeffrey D
authors.initials: JD
authors.lastname: St Denis
authors.affiliation: Davenport Research Laboratories, Department of Chemistry, University of Toronto , 80 St. George Street, Toronto, ON, M5S 3H6, Canada.
authors.forename: C Frank
authors.initials: CF
authors.lastname: Lee
authors.affiliation: Davenport Research Laboratories, Department of Chemistry, University of Toronto , 80 St. George Street, Toronto, ON, M5S 3H6, Canada.
authors.forename: Andrei K
authors.initials: AK
authors.lastname: Yudin
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000586:Amination; D001897:Boronic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry; D004952:Esters; D006867:Hydrolases / Q000037:antagonists & inhibitors / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism; D013451:Sulfonic Acids / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D001897:Boronic Acids; D004791:Enzyme Inhibitors; D004952:Esters; D013451:Sulfonic Acids; C005741:sulfamic acid; D012238:Rhodium; D006867:Hydrolases