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The oxidative dearomatization of resorcinol derivatives, which are outfitted with a lactic acid derived chiral tether, and mitigated by hypervalent iodine derivatives of PhIO, affords stable chiral cyclohexadienones as useful building blocks for the construction of many highly functionalized...
Both λ 3 - and λ 5 -iodanes have proven to be useful reagents in the oxygenative dearomatization of phenols, and exploitations of their chemistry in the conception of both substrate- and reagent-controlled asymmetric variants of such a transformation of great value for natural product synthesis...
Several transition metal-mediated oxidations using hypervalent iodine species are reported. A convenient procedure for preparation of iodylarenes via RuCl 3 -catalyzed oxidation of iodoarenes has been developed. This procedure allows the generation of highly reactive monomeric iodine(V) species,...
The addition of the hypervalent iodine reagent PIFA (phenyliodine(III) bis(trifluoroacetate)) to a series of properly substituted N -(3-aminopropyl)alkynylamides results in the efficient formation of a functionalized 5-aroyl-2-pyrrolidinone skeleton. By proper manipulations of the...
The synthesis and characterization of new hypervalent iodine reagents ArINTs ( 2a ), ArIO ( 3a ), and ArIO 2 ( 4a ) (Ar=2- tert -butylsulfonyl-5- tert -butylphenyl) are described. These reagents are compared to previously reported analogous set of reagents Ar=2- tert -butylsulfonylphenyl and...
Several new five- and a six-membered heterocyclic monochloroiodanes, including two cationic species, were synthesized. Three of which were used for the preparation of corresponding trifluoromethylation reagents. These compounds were characterized by X-ray crystallography for a comparative...
Functionalized bicyclo(3.3.1)non-3-en-2-ones are obtained from commercially available phenols by a hypervalent iodine oxidation, enone epoxidation, epoxide thiolysis, and intramolecular aldol reaction sequence. Reaction optimization studies identified room temperature as well as...
We first introduced 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) and 2,2,2-trifluoroethanol (TFE) as unique solvents for reactions involving hypervalent iodine-mediated phenolic oxidations in the 1980s, in which the fluoroalcohols have been successfully utilized as stabilizing solvents of the...
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