159249-15-7Relevant academic research and scientific papers
A multigram, catalytic and enantioselective synthesis of optically active 4-methyl-2-cyclohexen-1-one: A useful chiral building block
Bertozzi,Crotti,Feringa,Macchia,Pineschi
, p. 483 - 486 (2001)
The first catalytic asymmetric synthesis of both (R)-(+)- and (S)-(-)-4-methyl-2-cyclohexen-1-one and a new and improved synthesis of both enantiomers of (1S,4S)-(-) and (1R,4R)-(+)-4-methyl-2-cyclohexen-1-o1 was developed on a multigram scale. The key step of this approach is the asymmetric catalyzed addition of Me2Zn (SN2′-pathway) to racemic 1,3-cyclohexadiene monoepoxide. This step has been optimized as for as enantio- and regioselectivities, and work-up procedures. The striking ligand accelerated catalysis exhibited by the chiral copper complex of the 2,2′-binaphthyl-based phosphoramidite, herein reported, permitted a very low catalyst loading (0.6 mol%).
Copper-catalyzed highly enantioselective synthesis of cyclic allylic and homoallylic alcohols with dialkylzinc reagents
Pineschi, Mauro,Del Moro, Federica,Crotti, Paolo,Di Bussolo, Valeria,Macchia, Franco
, p. 334 - 337 (2007/10/03)
The copper-phosphoramidite catalyzed addition of dialkylzinc reagents to racemic or meso allylic epoxides can be synthetically exploited in different ways, depending on the substrates and reaction conditions used.
Catalytic Regiodivergent Kinetic Resolution of Allylic Epoxides: A New Entry to Allylic and Homoallylic Alcohols with High Optical Purity
Pineschi, Mauro,Del Moro, Federica,Crotti, Paolo,Di Bussolo, Valeria,Macchia, Franco
, p. 2099 - 2105 (2007/10/03)
A novel regiodivergent kinetic resolution of a series of allylic epoxides with alkylzinc reagents is described. Results demonstrate the potential of chiral copper-phosphoramidite catalysts for enantiomer differentiation of allylic epoxides, allowing a chiral catalyst-stereoregulated synthesis of cyclic allylic and homoallylic alcohols with high optical purities.
Enantioselective opening of cyclic vinyl epoxides with organoaluminium reagents catalysed by copper salts
Equey, Olivier,Alexakis, Alexandre
, p. 1531 - 1536 (2007/10/03)
Herein we report conditions for the enantioselective conjugate addition of trialkylaluminium reagents to cyclic vinyl epoxides catalysed by copper salts and chiral phosphorus-based ligands. The reaction must be carried out in THF, otherwise we observed only oligomeric products. The best ees have been obtained with CuTC as the copper salt and a 2,2′-binaphthyl-based phosphorus ligand. Both opening products (SN2 and SN2 ′ pathways) were obtained with good enantioselectivity and moderate to good regioselectivity.
