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Rhodium Carbenoid Initiated O–H Insertion/Aldol/Oxy-Cope Cascade for the Stereoselective Synthesis of Functionalized Oxacycles
journal contribution
posted on 2016-11-30, 15:20 authored by Kiran Chinthapally, Nicholas P. Massaro, Indrajeet SharmaA novel diazo-cascade approach has
been developed for the synthesis
of nine-membered oxacycles utilizing readily accessible β-hydroxy
vinyl ketones and vinyl diazo esters. The Rh(II)-catalyzed cascade
reaction begins with carbene O–H insertion followed by an intramolecular
aldol cyclization to provide a substituted tetrahydrofuran intermediate
that undergoes an oxy-Cope rearrangement to provide functionalized
nine-membered oxacycles with complete stereoselectivity.
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functionalized nine-membered oxacyclesFunctionalized OxacyclesStereoselective Synthesisinsertionoxy-Cope rearrangementRhRhodiumvinyl diazo estersInitiatedβ- hydroxy vinyl ketonesnovel diazo-cascade approachsynthesisnine-membered oxacyclestetrahydrofuranCascadestereoselectivityCarbenoidInsertionintramolecular aldol cyclizationcarbene
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