Exploring the Reactivity of Nitro-Activated 1,3-Enynes in an Organocatalytic One-Pot, Three-Component Coupling Reaction: A Tandem Catalytic Approach to a Novel 3-Nitrochroman Scaffold.

A tandem catalytic strategy enabling one-pot, three-component couplings of electron-rich phenols, 2-nitro 1,3-enynes, and vinyl ketones was achieved. This chemistry combined mechanistically distinct [3 + 3]-annulation and nitro-Michael addition using a single squaramide catalyst, leading to the construction of novel chiral quaternary 3-nitrochromane architecture with high chemo-, regio-, and stereoselectivity.