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.
Teng
Xin
X
Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA 02467, USA.
Cefalo
Dustin R
DR
Schrock
Richard R
RR
Hoveyda
Amir H
AH
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