The 1,1a,2,7b-tetrahydrocyclopropa[c]chromene, aris-ing 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 enantiose-lectivities and with perfect diastereoselectivity at the cyclopropane, using an alpha,alpha-diphenylprolinol aminocatalyst. The versatility of the hemiacetal moiety in the products was leveraged to effect various synthetic manipulations.
Bisag, G.D., Pecchini, P., Mancinelli, M., Fochi, M., Bernardi, L. (2022). Sulfoxonium Ylides in Aminocatalysis: An Enantioselective Entry to Cyclopropane-Fused Chromanol Structures. ORGANIC LETTERS, 24(29), 5468-5473 [10.1021/acs.orglett.2c02204].
Sulfoxonium Ylides in Aminocatalysis: An Enantioselective Entry to Cyclopropane-Fused Chromanol Structures
Bisag, Giorgiana Denisa;Pecchini, Pietro;Mancinelli, Michele;Fochi, Mariafrancesca
;Bernardi, Luca
2022
Abstract
The 1,1a,2,7b-tetrahydrocyclopropa[c]chromene, aris-ing 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 enantiose-lectivities and with perfect diastereoselectivity at the cyclopropane, using an alpha,alpha-diphenylprolinol aminocatalyst. The versatility of the hemiacetal moiety in the products was leveraged to effect various synthetic manipulations.File | Dimensione | Formato | |
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