All possible stereoisomers of imine derivatives 1 ± 4, which have the characteristic roast odor of seafood, were synthesized. As a result of odor evaluation of all isomers, we found that each isomer has a different and characteristic odor of roasted seafood.Introduction. ± Imine derivatives 1 ± 4 have the characteristic roast odor of seafood.

An abundant and low toxicity iron catalyst has enabled regioselective annulation of alkenes with α-halocarboxylic acids and their derivatives. The reaction proceeds smoothly without any additional ligands, bases, and additives to afford a variety of γ-lactones in good yields. A proposed reaction pathway through radical annulation is supported by some mechanistic studies, involving radical clock and isotope labeling experiments. The present method was applied to the practical iron-powder-promoted synthesis of γ-lactones.

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Copper-mediated [3 + 2] annulation of alkenes with α-nitrobenzyl bromides has been developed. The reaction is promoted simply by a copper salt to produce the corresponding 2-isoxazoline N-oxides with perfect regioselectivity. The present method can be conducted under mild conditions, affording a diverse array of 2-isoxazoline N-oxides. The obtained products can readily be converted to the related heterocycles such as 2-isoxazoline and isoxazole. A radical-polar crossover pathway initiated by single-electron transfer from nitronate to a copper salt is proposed.