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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Sulfoxonium Ylides in Aminocatalysis: An Enantioselective Entry to Cyclopropane-Fused Chromanol Structures
Giorgiana Denisa Bisag1, Pietro Pecchini1, Michele Mancinelli1
1Department of Industrial Chemistry "Toso Montanari", Center for Chemical Catalysis - C3, and INSTM RU Bologna, Alma Mater Studiorum - University of Bologna, V. Risorgimento 4, 40136 Bologna, Italy.
Abstract:
The 1,1a,2,7b-tetrahydrocyclopropa[c]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.
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