Organocatalytic Highly Enantioselective Monofluoroalkylation of 3‑Bromooxindoles: Construction of Fluorinated 3,3′-Disubstituted Oxindoles and Their Derivatives

A new practical organocatalytic asymmetric protocol for the introduction of a monofluoroalkyl group into the oxindole framework has been successfully developed. Excellent diastereoselectivities (>20:1 dr) and enantioselectivities (93–99% ee) of the products were obtained with a wide range of pre-electrophiles (3-bromooxindoles) and prenucleophiles (α-fluorinated β-keto <i>gem</i>-diols). The obtained products themselves and their derivatives may significantly benefit drug discovery

Base-Catalyzed Diastereoselective [3 + 3] Annulation of 3‑Isothiocyanatooxindoles and Azomethine Imines

An unprecedented diastereoselective [3 + 3] annulation of 3-isothiocyanatooxindoles and azomethine imines was catalyzed by Et₃N, affording 3,3′-triazinyl spirooxindoles in excellent yields and diastereoselectivities under mild conditions

Catalytic Kinetic Resolution of Spiro-Epoxyoxindoles with 1‑Naphthols: Switchable Asymmetric Tandem Dearomatization/Oxa-Michael Reaction and Friedel–Crafts Alkylation of 1‑Naphthols at the C4 Position

Switching the chemo- or regioselectivity from identical starting materials under readily tunable reaction conditions represents a great challenge in medicinal and synthetic organic chemistry. Herein, we report the asymmetric dearomatization/oxa-Michael reaction and Friedel–Crafts alkylation of 1-naphthols at the C4 position, wherein the chemoselectivity could be switched easily by using different reaction conditions without changing the catalyst and the substrates. The reactions feature asymmetric Friedel–Crafts alkylation of 1-naphthols at the C4 position and asymmetric dearomatization without using specific substrates or stepwise protocols

Catalytic Kinetic Resolution of Spiro-Epoxyoxindoles with 1‑Naphthols: Switchable Asymmetric Tandem Dearomatization/Oxa-Michael Reaction and Friedel–Crafts Alkylation of 1‑Naphthols at the C4 Position

Switching the chemo- or regioselectivity from identical starting materials under readily tunable reaction conditions represents a great challenge in medicinal and synthetic organic chemistry. Herein, we report the asymmetric dearomatization/oxa-Michael reaction and Friedel–Crafts alkylation of 1-naphthols at the C4 position, wherein the chemoselectivity could be switched easily by using different reaction conditions without changing the catalyst and the substrates. The reactions feature asymmetric Friedel–Crafts alkylation of 1-naphthols at the C4 position and asymmetric dearomatization without using specific substrates or stepwise protocols

Enantioselective Dearomative Arylation of Isoquinolines

The C1-substituted tetrahydroisoquinolines and 1,2-dihydroisoquinoline constitute an important group and are interesting structural motifs found in many natural products and pharmaceuticals. In this context, a phosphoric-acid-catalyzed enantioselective dearomative arylation of isoquinolines was realized, providing the chiral dihydroisoquinolines with indole substituents at the C1-position in good results (up to >99% yield and 97% ee). The reaction features mild reaction conditions and operational simplicity, which make it an attractive approach to the discovery of biologically interesting α-indolisoquinolines

Chiral Phosphoric Acid Catalyzed Asymmetric Oxidative Dearomatization of Naphthols with Quinones

A highly enantioselective oxidative dearomatization of naphthols with quinones catalyzed by a chiral spirocyclic phosphoric acid is described. The strategy provides concise access to enantioenriched cyclohexadienones with a quinone moiety. Remarkably, the obtained products could be easily transformed to a potentially useful dihydronaphtho­[2,1-<i>b</i>]­benzofuran scaffold