Iodine(III)-Mediated C-C Bond Coupling to Construct Spirocyclic Indolenines of Various Ring Sizes.

Herein, we report a novel iodine(III)-mediated intramolecular dearomative spirocyclization of indole derivatives to generate highly strained spirocyclobutyl, spirocyclopentyl, and spirocyclohexyl indolenines in moderate to good yields. A set of structurally novel, densely functionalized spiroindolenines with broad functional group compatibility was efficiently constructed in this way under mild reaction conditions. Moreover, the ß-enamine ester as a versatile functional group in the product provides great convenience for the synthesis of bioactive compounds and related natural products.

Highly regioselective ring-opening of epoxides with amines: a metal- and solvent-free protocol for the synthesis of ß-amino alcohols.

We herein report a metal- and solvent-free acetic acid-mediated ring-opening reaction of epoxides with amines. This process provides ß-amino alcohols in high yields with excellent regioselectivity. Importantly, this epoxide ring-opening protocol can be used for the introduction of amines in natural products during late-stage transformations.