Diastereocontrolled Construction of Spiroindolenines via Hexafluoroisopropanol-Promoted Dearomative Epoxide-Indole Cyclization.

Herein, we report the discovery of the ipso-selective, dearomatizing spirocyclization of indole-tethered epoxides as a fundamentally new approach for constructing spiroindolenines equipped with three contiguous stereogenic centers under complete diastereocontrol (dr >99:1) and in high yields. Promoted by hexafluoroisopropanol, the protocol features a broad substrate scope, easy scale-up, and versatile transformations of the synthesized spiroindolenines.

Expedient C-H allylation of sulfoxonium ylides: merging C-H and C-C/C-het bond activation.

Sulfoxonium ylide chelation-assisted C-H allylation of arenes has been accomplished utilizing strained vinyl carbo/heterocycles as the allyl surrogates via sequential C-H and C-C/het bond activation. Broad substrate scope, Co-catalysis, selectivity, and late-stage drug mutation are the important practical features.

Sc(OTf)3-Catalyzed Domino C-C/C-N Bond Formation of Aziridines with Quinones via Radical Pathway.

Sc(III)-catalyzed domino C-C and C-N bond formation of N-sulfonyl aziridines with quinones has been accomplished to furnish functionalized indolines at a moderate temperature. The umpolung reactivity of aziridines, radical pathway, mild reaction conditions, substrate scope, and coupling of drug molecules in a postsynthetic application are the important practical features.

Redox-Neutral Site-Selective C-H Allylation and Iodolactonization of Benzoic Acids Using Morita-Baylis-Hillman Adducts in Water.

A Ru-catalyzed carboxylate directed C-H allylation and iodolactonization of benzoic acids has been accomplished with Morita-Baylis-Hillman adducts as the coupling partner in environmentally benign water as solvent. The redox-neutral conditions, use of water as a solvent, substrate scope, functional group tolerance, and mutation of natural products and drug molecules are the important practical features.