Mechanistic analysis of an asymmetric palladium-catalyzed conjugate addition of arylboronic acids to β-substituted cyclic enones† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c4sc03337j Click here for additional data file.

Phosphine-catalyzed enantioselective [3 + 2] cycloadditions of γ-substituted allenoates with β-perfluoroalkyl enones† †Electronic supplementary information (ESI) available: Experimental details, analytical data, NMR spectra of products. CCDC 1503840 (3aa). For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7sc01432e Click here for additional data file. Click here for additional data file.

Stoichiometric to catalytic reactivity of the aryl cycloaurated species with arylboronic acids: insight into the mechanism of gold-catalyzed oxidative C(sp2)–H arylation† †Electronic supplementary information (ESI) available: Detailed experimental procedures, analytical data. CCDC 1000469, 1007212 and 1019879. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c4sc02070g Click here for additional data file. Click here for additional data file.

Asymmetric synthesis of functionalized cyclohexanes bearing five stereocenters via a one-pot organocatalytic Michael–Michael–1,2-addition sequence† †Electronic supplementary information (ESI) available. CCDC 990847. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c4cc01885k Click here for additional data file. Click here for additional data file.

A highly stereoselective one-pot procedure involving an enantioselective Michael addition promoted by low loading of an amino-squaramide catalyst followed by an achiral base catalyzed domino Michael-Knoevenagel-type 1,2-addition sequence provides efficient access to fully substituted cyclohexanes bearing five contiguous stereogenic centers in good yields (68-86%) and excellent stereoselectiviti...

Enantioselective palladium catalyzed conjugate additions of ortho-substituted arylboronic acids to β,β-disubstituted cyclic enones: total synthesis of herbertenediol, enokipodin A and enokipodin B.

The palladium-catalyzed conjugate addition (Michael addition) of ortho-substituted arylboronic acids to β,β-disubstituted cyclic enones, in particular 3-methyl cyclopent-2-enone and 3-methyl cyclohex-2-enone, is reported. With an achiral bipyridine-based palladium catalyst, good yields are obtained with a variety of ortho-substituted arylboronic acids. In the asymmetric version, good to very hi...

Mechanistic analysis of an asymmetric palladium-catalyzed conjugate addition of arylboronic acids to β-substituted cyclic enones

An asymmetric palladium-catalyzed conjugate addition reaction of arylboronic acids to enone substrates was investigated mechanistically. Desorption electrospray ionization coupled to mass spectrometry was used to identify intermediates of the catalytic cycle and delineate differences in substrate reactivity. Our findings provide evidence for the catalytic cycle proceeding through formation of a...