title: Rh-catalyzed addition of arylboroxines to cyclic N-(isopropanesulfinyl)ketimines.
abstract: 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.
authors.affiliation: Department of Chemistry, Yale University, New Haven, Connecticut 06520-8107, United States.
authors.forename: Hyung Hoon
authors.initials: HH
authors.lastname: Jung
authors.forename: Andrew W
authors.initials: AW
authors.lastname: Buesking
authors.forename: Jonathan A
authors.initials: JA
authors.lastname: Ellman