Enantioselective [4 + 2] cycloadditions of o-quinone methides: total synthesis of (+)-mimosifoliol and formal synthesis of (+)-tolterodine.
The first example of an enantioselective cycloaddition of an o-quinone methide (o-QM) with a chiral enol ether is described along with the total synthesis of (+)-mimosifoliol and the formal synthesis of (+)-tolterodine. These syntheses exemplify a three-component, one-pot benzopyran approach for the construction of chiral benzylic junctions. Cycloadditions of various enol ethers and o-QMs are examined, and diastereoselectivities >95% are obtained with trans-2-phenyl-1-cyclohexanol and 2,2-diphenylcyclopentanol vinyl ethers.
Selenski
Carolyn
C
Department of Chemistry and Biochemistry, University of California at Santa Barbara, California 93106-9150, USA.
Pettus
Thomas R R
TR
D000179:Acrylates / Q000138:chemical synthesis*; D001559:Benzhydryl Compounds / Q000138:chemical synthesis*; D003408:Cresols / Q000138:chemical synthesis*; D018360:Crystallography, X-Ray; D006139:Guaiacol / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D045563:Indolequinones / Q000737:chemistry*; D008958:Models, Molecular; D010665:Phenylpropanolamine / Q000138:chemical synthesis*; D013057:Spectrum Analysis; D013237:Stereoisomerism; D000068737:Tolterodine Tartrate
D000179:Acrylates; D001559:Benzhydryl Compounds; D003408:Cresols; D045563:Indolequinones; C102778:mimosifoliol; C068040:quinone methide; D010665:Phenylpropanolamine; D000068737:Tolterodine Tartrate; D006139:Guaiacol