154547-92-9Relevant academic research and scientific papers
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 (2000)
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.
Asymmetric Synthesis of 1,1-Disubstituted Tetralins and Dihydronaphthalenes by Diastereoselective Addition of Lithiosilanes to Chiral Naphthalenes
Hulme, Alison N.,Meyers, A. I.
, p. 952 - 953 (2007/10/02)
Highly diastereoselective additions of lithiosilanes to chiral naphthalenes can be performed in ether/THF.Trapping of the resulting azaenolate, followed by protodesilylation, allows access to 1,1-disubstituted tetralins or dihydronaphthalenes in good yields and high enantiomeric excess.
