title: Base-catalyzed bifunctional addition to amides and imides at low temperature. A new pathway for carbonyl hydrogenation.
abstract: Mono- or dideprotonation at the N-H groups of the Noyori ketone hydrogenation catalyst trans-[RuH2((R)-BINAP)((R,R)-dpen)] (1a) yields trans-M[RuH2((R,R)-HNCH(Ph)CH(Ph)NH2)((R)-BINAP)], where M = K(+)(8-K) or Li(+) (8-Li), or trans-M2[RuH2((R,R)-HNCH(Ph)CH(Ph)NH)((R)-BINAP)], where M = Li(+) (8-M'2), which have unprecedented activity toward the hydrogenation of amide and imide carbonyls at low temperatures in THF-d8. Details of the origins of the enantioselection for the desymmetrization of meso-cyclic imides by hydrogenation with 8-K are also described herein.
authors.affiliation: Department of Chemistry, University of Alberta, Edmonton, Alberta, Canada T6G 2G2.
authors.forename: Jeremy M
authors.initials: JM
authors.lastname: John
authors.forename: Satoshi
authors.initials: S
authors.lastname: Takebayashi
authors.forename: Nupur
authors.initials: N
authors.lastname: Dabral
authors.forename: Mark
authors.initials: M
authors.lastname: Miskolzie
authors.forename: Steven H
authors.initials: SH
authors.lastname: Bergens
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D000577:Amides / Q000737:chemistry*; D002384:Catalysis; D006865:Hydrogenation; D007094:Imides / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D012428:Ruthenium / Q000737:chemistry; D013237:Stereoisomerism; D013696:Temperature
chemical_list: D000438:Alcohols; D000577:Amides; D007094:Imides; D007659:Ketones; D009942:Organometallic Compounds; D012428:Ruthenium