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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
One-Pot Sulfoxide Synthesis Exploiting a Sulfinyl-Dication Equivalent Generated from a DABSO/Trimethylsilyl Chloride
Danny C Lenstra1, Vincent Vedovato1, Emmanuel Ferrer Flegeau1
1Department of Chemistry, University of Oxford , Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, United Kingdom.
Abstract:
A one-pot process for the synthesis of unsymmetrical sulfoxides using organometallic nucleophiles is described. Sulfur dioxide, delivered from the surrogate DABSO (DABCO-bis(sulfur dioxide)), acts as the initial electrophile and combines with the first organometallic reagent to generate a sulfinate intermediate. In situ conversion of the sulfinate to a sulfinate silyl ester, using TMS-Cl (trimethylsilyl chloride), generates a second electrophile, allowing addition of a second organometallic reagent. Organolithium or Grignard reagents can be employed, delivering sulfoxides in good to excellent yields.
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