Monofluorocyclohexanols 1 are obtained in optically pure form through radical cyclization of gem-chlorofluoroheptenols 2 which derive front the condensation of alpha-lithium derivative of sulfoxide 3 on racemic ethyl chlorofluoroacetate 4, and hydride-promoted reduction of the intermediate ketones 5. Some considerations on the stereochemical course of the radical promoted cyclization reaction follow.
ON THE SYNTHESIS OF OPTICALLY PURE MONOFLUOROCYCLOHEXANOL DERIVATIVES BY THE FLUORINATED SULFOXIDE CHIRON ROUTE
CRUCIANELLI, MARCELLO
1994-01-01
Abstract
Monofluorocyclohexanols 1 are obtained in optically pure form through radical cyclization of gem-chlorofluoroheptenols 2 which derive front the condensation of alpha-lithium derivative of sulfoxide 3 on racemic ethyl chlorofluoroacetate 4, and hydride-promoted reduction of the intermediate ketones 5. Some considerations on the stereochemical course of the radical promoted cyclization reaction follow.File in questo prodotto:
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