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A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Interrupted Corey-Chaykovsky Reaction of Tethered Bis-Enones to Access 2,3-Epoxy-hexahydrofluoren-9-ones
Jay Prakash Maurya1, S S V Ramasastry1
1Department of Chemical Sciences, Indian Institute of Science Education and Research (IISER) Mohali, Sector 81 S A S Nagar, Manauli PO, Punjab 140 306, India.
Abstract:
The Corey-Chaykovsky reaction is usually employed to synthesize cyclopropanes from activated olefins. We intercepted the intermediates prevailing during this transformation and diverted the process for the creation of intricate molecular motifs. We describe an unusual skeletal remodelling of tethered bis-enones to 2,3-epoxy-hexahydrofluoren-9-ones via an "interrupted Corey-Chaykovsky reaction". The strategy rationally merges the nucleophilic features of sulfur ylides with electronically biased olefins to achieve the regio- and stereoselective synthesis of several new classes of hydrofluorenones. We have demonstrated the synthetic utility of the products in accessing several highly functionalized molecules.
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