Efficient catalytic enantioselective synthesis of unsaturated amines: preparation of small- and medium-ring cyclic amines through mo-catalyzed asymmetric ring-closing metathesis in the absence of solvent.
The first catalytic asymmetric ring-closing metathesis method for the synthesis of N-containing heterocycles is reported; this is accomplished through Mo-catalyzed kinetic resolution or desymmetrization of unsaturated amines. Importantly, this catalytic asymmetric method delivers medium-ring unsaturated amines (including eight-membered rings) in high yield, with exceptional enantioselectivity and without the need for solvents. These enantioselective reactions can be effected by catalysts prepared in situ from commercially available reagents.
Dolman
Sarah J
SJ
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Sattely
Elizabeth S
ES
Hoveyda
Amir H
AH
Schrock
Richard R
RR
D000588:Amines / Q000138:chemical synthesis*; D002384:Catalysis; D006844:Hydrocarbons, Cyclic / Q000737:chemistry; D007700:Kinetics; D008982:Molybdenum / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry; D012997:Solvents; D013237:Stereoisomerism
D000588:Amines; D006844:Hydrocarbons, Cyclic; D009942:Organometallic Compounds; D012997:Solvents; D008982:Molybdenum