Journal ArticleDOI
Efficient oxidation of phenyl groups to carboxylic acids with ruthenium tetraoxide. A simple synthesis of (R-γ-caprolactone, the pheromone of Trogoderma granarium).
M. T. Nunez,V. S. Martin +1 more
TLDR
In this article, a simple synthesis of (R)-γ-caprolactone employing Sharpless asymmetric epoxidation and the presented oxidation procedure as key steps is presented. But the procedure is compatible with other functional groups except for those that are quite acid sensitive.Abstract:
The oxidation of aromatic rings to carboxylic acids with ruthenium tetraoxide is shown to be a very efficient and simple reaction using periodic acid as the stoichiometric oxidant in a biphasic solvent system (CCl 4 , CH 3 CN, H 2 O). The reaction can be very sensitive to the nature of the ring substituents when more than one aromatic ring is present. The procedure is compatible with other functional groups except for those that are quite acid sensitive. A simple synthesis of (R)-γ-caprolactone employs Sharpless asymmetric epoxidation and the presented oxidation procedure as key stepsread more
Citations
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Ruthenium-Catalyzed Reactions for Organic Synthesis.
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Enantioselective Mukaiyama-aldol and aldol-dihydropyrone annulation reactions catalyzed by a tryptophan-derived oxazaborolidine
TL;DR: The (S)-tryptophan derived catalyst has been used to effect enantioselective Mukaiyama-aldol and aldol-dihydropyrone annulation reactions of trimethylsilyloxy olefins and dienes.
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Lewis base activation of Lewis acids: catalytic, enantioselective addition of silyl ketene acetals to aldehydes.
TL;DR: The high levels of regio-, anti diastereo-, and enantioselectivity observed in these reactions can be rationalized through consideration of an open transition structure where steric interactions between the silyl cation complex and the approaching nucleophile are dominant.
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Ruthenium‐Catalyzed cis‐Dihydroxylation of Alkenes: Scope and Limitations
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Chromium(VI) oxide catalyzed oxidation of sulfides to sulfones with periodic acid
TL;DR: A highly efficient and selective oxidation of sulfides to sulfones with periodic acid catalyzed by CrO(3) is described.