title: Highly enantioselective Rh-catalyzed alkenylation of imines: synthesis of chiral allylic amines via asymmetric addition of potassium alkenyltrifluoroborates to N-tosyl imines.
abstract: For the first time, simple N-tosyl aryl aldimines, prepared from the condensation of tosyl amide and aromatic aldehydes, can be used as substrates in the rhodium catalyzed 1,2-addition reaction using alkenylboron nucleophiles. In the presence of 1.5 mol % of [RhCl(1e)]2, enantioselective addition of various potassium alkenyltrifluoroborates to aryl aldimines furnished the corresponding chiral allylic amines in 73-96% yield and 72->99.5% ee. Notably, this method efficiently provides the di-, tri-, and tetrasubstituted allylic N-tosyl amines with high asymmetric induction.
authors.affiliation: Department of Chemistry and Instrumentation Center, National Taiwan Normal University , No. 88, Section 4, Tingzhou Road, Taipei, 11677, Taiwan, Republic of China.
authors.forename: Balraj
authors.initials: B
authors.lastname: Gopula
authors.forename: Chien-Wei
authors.initials: CW
authors.lastname: Chiang
authors.forename: Way-Zen
authors.initials: WZ
authors.lastname: Lee
authors.forename: Ting-Shen
authors.initials: TS
authors.lastname: Kuo
authors.forename: Ping-Yu
authors.initials: PY
authors.lastname: Wu
authors.forename: Julian P
authors.initials: JP
authors.lastname: Henschke
authors.forename: Hsyueh-Liang
authors.initials: HL
authors.lastname: Wu
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D001881:Borates / Q000737:chemistry*; D002384:Catalysis; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000588:Amines; D001881:Borates; D007097:Imines; D012238:Rhodium