Abstract
A highly regio- and diastereoselective cascade formal nucleophilic substitution and Mannich reaction of ethyl 2-aroyl-1-chlorocyclopropanecarboxylates with salicylaldimines is described. Under basic conditions, ethyl 2-aroyl-1-chlorocyclopropanecarboxylate is easily converted into a cyclopropene intermediate via simple 1,2-elimination of hydrogen chloride. The highly reactive cyclopropene quickly combines with salicylaldimine through regioselective oxa-addition to the strained C═C bond and subsequent diastereoselective addition to C═N bond, constructing C–O and C–C bonds at one time. This provides a highly stereoselective novel methodology for synthesis of conformationally constrained cis-tetrahydrocyclopropa[b]chromene derivatives.
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