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Thegeneral and efficient palladium-catalyzed indium-mediated allylationof chiral hydrazones was accomplished with excellent yield (72–92%)and diastereoselectivity (up to 99:1). The development of this reactionand the substrate scope are described. The conversion was found tobe proportional to the phosphine concentration, which provided insightinto the mechanism and competing pathways of the redox transmetalationprocess. [ABSTRACT FROM AUTHOR]

A convenient and efficient procedure for the synthesis of β-alkyl/arylsulfanyl carbonyl compounds has been developed by a simple one-pot reaction of dialkyl/diaryl sulfides with α,β-unsaturated aldehydes, ketones, carboxylic esters, and nitriles in presence of indium and trimethylsilyl chloride under sonication. [ABSTRACT FROM AUTHOR]

Diphenyl diselenides and disulfides undergo facile cleavages by indium(I) iodide and the corresponding generated selenate and thiolate anions condense in situ with alkyl or acyl halides present in the reaction mixture. Thus, a simple, efficient, and general procedure has been developed for the synthesis of unsymmetrical diorganyl selenides, sulfides (thioethers), selenoesters, and thioesters by this one-pot reaction at room temperature. [ABSTRACT FROM AUTHOR]

In the title compound, C(10)H(22)NO(6)P, a staggered conformation is found when the mol-ecule is viewed down the central P-C bond, with the oxo and hydr-oxy groups gauche to each other. The crystal structure features supra-molecular chains of helical topology propagating along the b axis, mediated by O-H⋯O hydrogen bonds.

In the title compound, C(14)H(21)FNO(6)P, a staggered conformation about the central P-C bond occurs, with the oxo and hydroxyl groups occupying diagonally opposite positions. The crystal structure features supra-molecular chains mediated by O-H⋯O hydrogen bonds, which propagate in the a-axis direction. A C-H⋯O inter-action consolidates the chains. Disorder was resolved for one of the isopropyl groups with a 0.60 (2):0.40 (2) occupancy ratio for the two components.

Some novel prolinal dithioacetal derivatives were studied as catalysts for the inverse-electron-demand hetero-Diels-Alder reaction of enolizable aldehydes and beta,gamma-unsaturated alpha-ketophosphonates. The corresponding 5,6-dihydro-4H-pyran-2-ylphosphonates were obtained in good ee values (up to 94% ee).

[reaction: see text] The first organocatalytic highly enantioselective nitroaldol reaction of alpha-ketophosphonates and nitromethane has been realized by using cupreine (2) or 9-O-benzylcupreine (3) as the catalyst. Both catalysts are highly reactive and highly enantioselective. alpha-Hydroxy-beta-nitrophosphonates have been synthesized in good yields and excellent enantioselectivities (>or=90% ee) at a low catalyst loading (5 mol %). These nitroaldol products may be reduced to the biologically significant beta-amino-alpha-hydroxyphosphonates with complete retention of the stereochemistry.

A simple and efficient procedure has been developed for the synthesis of unsymmetrical diorganyl selenides through a one-pot indium(I) iodide-mediated reaction of alkyl halide and diphenyl diselenide in methylene chloride at room temperature. [reaction: see text]