501657-49-4Relevant academic research and scientific papers
Palladium-catalyzed asymmetric allylic alkylation of α-aryl ketones
Trost, Barry M.,Schroeder, Gretchen M.,Kristensen, Jesper
, p. 3492 - 3495 (2002)
Quaternary centers can be created asymmetrically in high enantiomeric excess by the proper choice of ligand and metal cation in the Pd-catalyzed asymmetric allylic alkylation of α-aryl ketones. A broad range of ketone enolates can be tolerated in the reac
Enantioselective synthesis of rigid 2-aminotetralins. Utility of silicon as an oxygen and nitrogen surrogate in the tandem addition reaction
Degnan, Andrew P.,Meyers
, p. 3503 - 3512 (2007/10/03)
Dimethylphenylsilyllithium undergoes a highly diastereoselective conjugate addition to chiral naphthyloxazoline 11. Electrophilic trapping of the resulting aza-enolate affords the tandem addition product (12) in high yields as a single diastereomer. The silicon, thus incorporated, may be protodesilylated and undergoes a Tamao oxidation to afford the corresponding alcohol. By chemical modification of the oxazoline, both the γ-lactone (28) and the δ-lactone (37) were prepared. Reduction of each lactone followed by oxidation of the ensuing diol gave the keto aldehyde. Double reductive animation of the 1,4-dicarbonyl (from the γ-lactone) allowed the synthesis of two novel hexahydrobenz[e]indoles, 20 and 35. Double reductive amination of the 1,5-dicarbonyl (from the δ-lactone) gave access to two novel octahydrobenzo[f]quinolines, 41 and 43. An unprecedented rearrangement of nitro alcohol 26 into lactone 28 is described and a reasonable mechanism for its formation postulated.
