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Abstract: A convenient enantioselective synthesis of 3-asymmetrically substituted oxindoles is reported. Compound (2) prepared by radical cyclisation of (1) was used for the synthesis of racemic and enantiomerically pure 3-asymmetrically substituted oxindoles. Desulfurisation of (2) using Raney Ni yielded the racemate (5). Addition of (S)-1-phenylethanol to compound (2) yielded the diastereoisomer (21) the structure of which was determined using X-ray crystallography. Using a sequence of steps (21) was converted to the enantiomer (8). The enantiomer (9) was similarly prepared from (2) using (R)-1-phenylethanol. [Copyright &y& Elsevier]

Abstract: Compound 4 prepared from Isatin in two steps underwent an unusual radical-induced rearrangement reaction to yield 9 as the major product and 10 as the minor component. Compound 9 shows structural similarities to the antimitotic agent rhazinilam and the gamma secretase inhibitor LY411575. The scope of the reaction has been studied by changing the substitutions on the aromatic rings and the mechanism for the formation of 9 and 10 from 4 is suggested. [Copyright &y& Elsevier]

Abstract: This paper describes a novel synthetic route for the preparation of ortho–ortho disubstituted biphenyls and compounds possessing highly condensed ring system represented by structures X and Y, respectively. Several approaches, such as intermolecular Grubb''s olefin metathesis, Heck and, Suzuki reactions were incorporated to functionalize the core structures of X and Y making it suitable for the preparation of a library of compounds. [Copyright &y& Elsevier]