34737-39-8Relevant articles and documents
A short access to (+)-ptilocaulin
Cossy, Janine,BouzBouz, Samir
, p. 5091 - 5094 (1996)
A short access to (+)-ptilocaulin involving a photoreductive cyclopropane ring opening of an optically active bicyclo(4.1.0)heptanone derivative is described.
Formation of contiguous quaternary and tertiary stereocenters by sequential asymmetric conjugate addition of grignard reagents to 2-substituted enones and mg-enolate trapping
Germain, Nicolas,Alexakis, Alexandre
, p. 8597 - 8606 (2015/06/02)
Herein a comprehensive study is provided on the asymmetric conjugate addition (ACA) of Grignard reagents to α-substituted cyclic enones. After the elucidation of the optimal experimental conditions, the scope of Grignard reagents and Michael acceptors was examined. Whereas secondary Grignards gave better enantioselectivities with 2-cyclopentenones, both linear and branched Grignard reagents were tolerated for the ACA to 2-methylcyclohexenone. The sequential ACA-enolate trapping, which leads to quaternary stereocenters, was then studied. Thus, many electrophiles have been tested, thereby giving rise to highly functionalized cyclic ketones with contiguous α-quaternary and β-tertiary centers. The present technique is believed to bring a new approach to versatile terpenoid-like skeletons of bioactive natural products. Straightforward derivatizations of enantioenriched saturated cyclic ketones further support the potential of the present methodology in synthesis.
Copper/palladium-catalyzed 1,4 reduction and asymmetric allylic alkylation of α,β-unsaturated ketones: Enantioselective dual catalysis
Nahra, Fady,Mace, Yohan,Lambin, Dominique,Riant, Olivier
supporting information, p. 3208 - 3212 (2013/04/23)
Cooperative efforts: The catalytic coupling of the two organometallic intermediates is possible through a Cu/Pd-based dual catalysis (see scheme; LG=leaving group), in which the CuI catalytic cycle generates catalytically the starting material
