One-Step Syntheses of 3,4-Disubstituted Isochroman-1-ones by the Annulation of Benzoic Acids with Nitroalkenes.

ABSTRACT

The Rh(III)-catalyzed annulation of benzoic acids with nitroalkenes was disclosed to afford a wide range of 3,4-disubstituted isochroman-1-ones with excellent regioselectivity and high catalytic efficiency. Both aromatic and aliphatic nitroalkenes participated in this cyclization reaction successfully. The synthetic value of 3,4-disubstituted isochroman-1-ones was proven by a series of derivatizations. Furthermore, a reliable mechanism is outlined on the basis of experimental investigations and related precedents.