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Abstract:The Rh 2 (OAc) 4 -catalyzed oxonium ylide formation-[2,3]-sigmatropic rearrangement of a highly functionalized α-diazo-β-keto ester derived from D-glucose proceeded stereoselectively to give the corresponding tetrahydrofuran-3-one as a single diastereomer in high yield. This reaction was applied to the synthesis of 2-epi-cinatrin C 1 dimethyl ester as a key step.

Novel bifunctional hybrid-type catalysts bearing 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) and iodobenzene moieties (1a and 1b) were developed and used for the environmentally benign oxidation of primary alcohols to carboxylic acids. Reaction of primary alcohols 2 with a catalytic amount of 1 in the presence of peracetic acid as a co-oxidant under mild conditions gave the corresponding carboxylic acids 3 in excellent yields.

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Novel 2,2,6,6-Tetramethylpiperidine 1-Oxyl-Iodobenzene Hybrid Catalyst for Oxidation of Primary Alcohols to Carboxylic Acids. -A variety of primary and secondary alcohols is oxidized to carboxylic acids with mostly small amounts of aldehydes using the hybrid catalysts (I) and large excess of peracetic acid. Aliphatic alcohols require larger catalyst loading. -(YAKURA*, T.; OZONO, A.; Adv. Synth. Catal. 353 (2011) 6, 855-859, http://dx.doi.org/10.1002/adsc.201100024 ; Grad. Sch. Med. Pharm. Sci., Univ. Toyama, Toyama 930, Japan; Eng.) -Y. Steudel 36-075