283585-40-0

Upstream product

• 283584-97-4 (S)-4-tert-Butyl-2-[(1S,2S)-2-(dimethyl-phenyl-silanyl)-1-methyl-1,2,3,4-tetrahydro-naphthalen-1-yl]-4,5-dihydro-oxazole 
• 132912-17-5 1-<4'-(S)-tert-butyloxazolin-2'-yl>naphthalene 
• 283585-04-6 (1S,2S)-2-(Dimethyl-phenyl-silanyl)-1-methyl-1,2,3,4-tetrahydro-naphthalene-1-carbaldehyde 
• 154547-92-9 (S)-4-tert-Butyl-2-[(1S,2S)-2-(dimethyl-phenyl-silanyl)-1-methyl-1,2-dihydro-naphthalen-1-yl]-4,5-dihydro-oxazole 
• 154547-98-5 (1S,2S)-2-(Dimethyl-phenyl-silanyl)-1-methyl-1,2-dihydro-naphthalene-1-carbaldehyde 
• 768-33-2 phenyldimethylsilyl chloride 

Downstream Products

• 283585-51-3 (4aR,10bR)-10b-Methyl-4-((R)-1-phenyl-ethyl)-1,2,3,4,4a,5,6,10b-octahydro-benzo[f]quinoline 
• 283585-49-9 (4aS,10bR)-10b-Methyl-4-((S)-1-phenyl-ethyl)-1,2,3,4,4a,5,6,10b-octahydro-benzo[f]quinoline 

Relevant 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

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.