120523-13-9Relevant academic research and scientific papers
Regiocontrol by Remote Substituents. A Direct Total Synthesis of Racemic Hongconin
Kraus, George A.,Li, Jun,Gordon, Mark,Jensen, Jan H.
, p. 2219 - 2222 (1994)
The total synthesis of hongconin (1) has been completed.Key steps include the metalation of a benzylic alcohol, the formation of a six-membered ring ether via a mercury-mediated cyclization, and the regioselective installation of the naphthalene ring by way of a Diels-Alder reaction.
RETRACTED ARTICLE: The Manganese(I)-Catalyzed Asymmetric Transfer Hydrogenation of Ketones: Disclosing the Macrocylic Privilege
Passera, Alessandro,Mezzetti, Antonio
supporting information, p. 187 - 191 (2019/12/11)
The bis(carbonyl) manganese(I) complex [Mn(CO)2(1)]Br (2) with a chiral (NH)2P2 macrocyclic ligand (1) catalyzes the asymmetric transfer hydrogenation of polar double bonds with 2-propanol as the hydrogen source. Ketones (43 substrates) are reduced to alcohols in high yields (up to >99 %) and with excellent enantioselectivities (90–99 % ee). A stereochemical model based on attractive CH–π interactions is proposed.
Rh(I)-catalysed asymmetric hydrosilylation using new oxazoline ligands with potential charge-transfer properties
Brunner, Henri,Stoeriko, Reinhard
, p. 783 - 788 (2007/10/03)
Novel N′-methylated 2-(oxazolin-2-yl)-4,4′-bipyridinium salts, bearing a chiral oxazoline moiety, were tested in the Rh(I)-catalysed enantioselective hydrosilylation. After coordination to rhodium these electron-attracting ligands are supposed to exhibit charge-transfer effects with electron-donating substrates. Therefore, a new catalytic hydrosilylation reaction with 2,5-dimethoxyacetophenone as an electron-rich substrate was developed. The results were compared with those of the non-methylated 2-(oxazolin-2-yl)-4,4′-bipyridine and related ligands. In addition, the new ligands and Rh(I)-complexes were tested in the hydrosilylation of acetophenone.
A Reinvestigation of the Meerwein-Ponndorf-Verley Reduction: A Highly Efficient Variation Using Zirconium Catalysts
Knauer, Birgit,Krohn, Karsten
, p. 677 - 684 (2007/10/02)
A new variation of the Meerwein-Ponndorf-Verley reduction based on mechanistic considerations is presented.Under optimized conditions 1-(4-dimethylaminophenyl)ethanol was used as the reducing alcohol (2-4 equiv.), Zr(O-tBu)4 as the catalyst (0.2 equiv.), and toluene or cyclohexane as the solvent.Aldehydes and ketones (if not extremely sterically hindered) were reduced to the corresponding alcohols at room temperature mostly within 2-4 h in essentially quantitative yield. α,β-Unsaturated carbonyl compounds cleanly react in a 1,2-mode to afford the corresponding allylic alcohols. - Key Words: Reductions / Meerwein-Ponndorf-Verley reaction / Catalysis / Zirconium tetra-tert-butoxide / β-Hydride shift / Kinetics
DEOXYGENATION OF ALDEHYDES AND KETONES WITH SODIUM CYANOBOROHYDRIDE
Elliger, Carl A.
, p. 1315 - 1324 (2007/10/02)
Treatment of hydroxy-substituted aromatic aldehydes and ketones with sodium cyanoborohydride yields the corresponding methylene compounds under conditions which favor intermediate carbonium ion formation.
