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An enantio- and diastereoselective syntheses of 1, 3-disubstituted isoindolines and tetrahydroisoquinolines via CuI-Pybox-diPh catalyzed one-pot imination–alkynylation–aza-Michael sequence has been reported. The three-component reaction produces one C–C and two C–N bonds sequentially with high yield (up to 92%), enantioselectivity (up to 99%), and diastereoselectivity (up to 9:1) in a single operation. Furthermore, the synthetic utility of the product has been demonstrated by LiAlH4 reduction of ester and hydrogenation of alkyne functionality without losing the stereoselectivity.

The first stereoselective propargylic dearomatization of 2-naphthol derivatives is reported using a chiral CuII–L10 complex. The reaction shows chemodivergent reactivity and produced propargyl dearomatization and etherification product for differently substituted 2-naphthols. Both the reactions generate the desired products in high yields with excellent chemo- and stereoselectivities (up to 99% ee, dr = 9:1) by using only 2 mol % catalyst loading. Dearomatization products contain a contiguous all-carbon quaternary–tertiary stereocenter and a terminal alkyne functionality.

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Various title compounds of type (III) (20 examples) are prepared in order to test their diuretic and hypoglycemic activity.