Sulfoxonium Ylides in Aminocatalysis: An Enantioselective Entry to Cyclopropane-Fused Chromanol Structures
Giorgiana Denisa Bisag, Pietro Pecchini, Michele Mancinelli, Mariafrancesca Fochi, Luca Bernardi
Abstract
]chromene, arising from fusion of chromane and cyclopropane rings is the core of medicinally relevant compounds. Engaging sulfoxonium ylides in enantioselective aminocatalytic reactions for the first time, a convenient entry to this scaffold is presented. Several ring-fused derivatives were obtained in moderate-to-good yields and enantioselectivities and with perfect diastereoselectivity at the cyclopropane, using an α,α-diphenylprolinol aminocatalyst. The versatility of the hemiacetal moiety in the products was leveraged to effect various synthetic manipulations.
Topics & Concepts
CyclopropaneEnantioselective synthesisChemistryRing (chemistry)MoietyStereochemistryCombinatorial chemistryOrganic chemistryCatalysisCyclopropane Reaction MechanismsSynthesis and Catalytic ReactionsAsymmetric Synthesis and Catalysis