Enantioselective synthesis of medium-ring heterocycles, tertiary ethers, and tertiary alcohols by Mo-catalyzed ring-closing metathesis.
The Mo-catalyzed asymmetric ring-closing metathesis (ARCM) of various achiral trienes leads to the formation of medium-ring unsaturated heterocycles in high yield and with excellent enantioselectivity. Reactions may be carried out on gram scale and in the absence of solvent. The unsaturated siloxanes obtained enantioselectively can be readily functionalized to obtain synthetically useful and difficult-to-access tertiary alcohols.
Kiely
Andrew F
AF
Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA 02467, USA.
Jernelius
Jesper A
JA
Schrock
Richard R
RR
Hoveyda
Amir H
AH
D000438:Alcohols / Q000138:chemical synthesis*; D002384:Catalysis; D004988:Ethers, Cyclic / Q000138:chemical synthesis*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D006844:Hydrocarbons, Cyclic / Q000138:chemical synthesis*; D008982:Molybdenum / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D000438:Alcohols; D004988:Ethers, Cyclic; D006571:Heterocyclic Compounds; D006844:Hydrocarbons, Cyclic; D009942:Organometallic Compounds; D008982:Molybdenum