Synthesis and Applications - The Anderson Research Group
Synthesis and Applications - The Anderson Research Group
Synthesis and Applications - The Anderson Research Group
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Carbon-Oxygen Bond Formations<br />
Tamao-Fleming Oxidations<br />
One-Pot Hydrosilylation-Oxidation<br />
<strong>The</strong> Trost group has developed a one-pot conversion of propargylic alcohols to β-hydroxyketones.<br />
BDMS readily forms the silanol when treated with TBAF. Intramolecular trapping<br />
with the free alcohol is believed to form an endocyclic vinyl siloxane intermediate.<br />
Elaboration of this methodology <strong>and</strong> use of enantiomerically-enriched propargylic alcohols<br />
provides an entry point to stereochemically well-defined α,β-hydroxylketones <strong>and</strong> epoxy<br />
alcohols.<br />
One-Pot: Trost, B.M.; Ball, Z.T.; Joge, T. Angew. Chem. Int. Ed. 2003, 42, 3415-3418.<br />
Epoxidation & Elaboration: Trost, B.M.; Ball, Z.T.; Laemmerhold, K.M. J. Am. Chem. Soc. 2005, 127, 10028-10038.
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