Enhancement of enantioselectivity by THF in asymmetric mo-catalyzed olefin metathesis. Catalytic enantioselective synthesis of cyclic tertiary ethers and spirocycles.
Mo-catalyzed enantioselective rearrangement of achiral cyclopentenyl tertiary ethers to chiral cyclohexenyl tertiary ethers are reported. These olefin metathesis transformations proceed efficiently and with high levels of enantioselectivity. A noteworthy feature of these reactions is that added tetrahydrofuran exerts a remarkably positive influence on the enantioselectivity of the metathesis-based rearrangement. The first examples of catalytic asymmetric synthesis of spirocyclic structures by enantioselective olefin metathesis are also disclosed.
Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA 02467, USA.
Xin
X
Teng
Dustin R
DR
Cefalo
Richard R
RR
Schrock
Amir H
AH
Hoveyda
D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D004988:Ethers, Cyclic / Q000138:chemical synthesis*; D005663:Furans / Q000737:chemistry*; D008982:Molybdenum / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry; D012997:Solvents; D013141:Spiro Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013379:Substrate Specificity
D000475:Alkenes; D004988:Ethers, Cyclic; D005663:Furans; D009942:Organometallic Compounds; D012997:Solvents; D013141:Spiro Compounds; C018674:tetrahydrofuran; D008982:Molybdenum