Organocatalytic asymmetric chlorinative dearomatization of naphthols.

Organocatalytic asymmetric chlorinative dearomatization of naphthols† †Electronic supplementary information (ESI) available: Experimental procedures and analysis data for the new compounds. CCDC 1048128 ((R)-2t) and 1048302 ((R)-2d). For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5sc00494b

Catalytic asymmetric hydroxylative dearomatization of 2-naphthols: synthesis of lacinilene derivatives.

An enantioselective hydroxylative dearomatization of 2-naphthols with oxaziridines has been accomplished using a N,N'-dioxide-scandium(iii) complex catalyst. Various substituted ortho-quinols could be obtained in high yields (up to 99%) and enantioselectivities (up to 95 : 5 er). This methodology could be applied in the synthesis of bioactive lacinilenes in a gram-scale reaction. Based on the e...

Catalytic asymmetric hydroxylative dearomatization of 2-naphthols: synthesis of lacinilene derivatives† †Electronic supplementary information (ESI) available. CCDC 1536822. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7sc02809a Click here for additional data file. Click here for additional data file.

An enantioselective organocatalytic oxidative dearomatization strategy.

The inherent reactivity and functionality stored within aromatic systems provide numerous possibilities for the synthesis of 3-D organic structures via dearomatization processes.1,2 Under oxidizing conditions, the dearomatization of orthoand para-substituted phenols forms cyclohexadienones,3 and these products have found widespread use in the chemical synthesis of natural products.4 Additionall...

Stereoselective α-indolylation of enals via an organocatalytic formal cross-coupling with indoles.

We report a novel organocatalytic one-pot cascade bromination-Michael-type Friedel-Crafts alkylation dearomatization-nucleophilic rearrangement aromatization cascade process for the direct α-indolylation of unfunctionalized enals from readily available indoles with good yields and high E selectivity. The simplicity and practicality of its high efficiency for formation of a new C(sp(2))-C(sp(2))...