ja0469075_si_001.pdf (4.61 MB)
Synthesis of Diastereomerically and Enantiomerically Pure 2,3-Disubstituted Tetrahydrofurans Using a Sulfoxonium Ylide
journal contribution
posted on 2004-10-27, 00:00 authored by Jennifer M. Schomaker, Veera Reddy Pulgam, Babak BorhanNucleophilic substitution reactions of 2,3-epoxy alcohols, easily prepared via Sharpless asymmetric epoxidation chemistry, offer access to a wide variety of enantiomerically pure compounds. In this communication, we describe the use of a Payne rearrangement to control regioselectivity in the ring-opening of a series of 2,3-epoxy alcohols with dimethylsulfoxonium methylide to yield diastereomerically and/or enantiomerically pure disubstituted tetrahydrofuran rings. The factors influencing the success and substitution pattern of the THF ring products are discussed, including steric, electronic, and solvent effects.
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compoundcommunicationepoxidation chemistryPurefactorstericenantiomericallyTetrahydrofuranTHF ring productsdimethylsulfoxonium methylideseriesSharplesSulfoxonium Ylide Nucleophilic substitution reactionsoffer accessDiastereomericallyDisubstitutedcontrol regioselectivitydisubstituted tetrahydrofuran ringsdiastereomericallyvarietySynthesisubstitution patternEnantiomericallyPayne rearrangement
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