201739-25-5

Upstream product

• 194233-66-4 (1E)-3-{[tert-butyl(dimethyl)silyl]oxy}-N,N-dimethyl-1,3-butadien-1-amine 
• 253665-35-9 (1S,2R,4R,S_S)-7,7-dimethyl-N-(phenylmethylene)-2-(trimethylsilyloxy)bicyclo[2.2.1]heptane-1-methanesulfinamide 
• 350479-90-2 (S,E)-N-benzylidene-4-methylbenzenesulfinamide 
• 173606-56-9 4-oxo-2-phenyl-3,4-dihydro-2H-pyridine-1-carboxylic acid methyl ester 
• 1240530-47-5 (R)-tert-butyl 3-oxo-1-phenylpent-4-ynylcarbamate 

Downstream Products

• 201739-26-6 C₃₀H₂₄N₂O₄ 
• 201739-27-7 (6R,8aR,8bS,11R,11bS,11cR)-6,11-Diphenyl-6,7,8a,8b,10,11,11b,11c-octahydro-5a,11a-diaza-benzo[6,7]cycloocta[1,2,3,4-def]biphenylene-5,8,9,12-tetraone 

Relevant academic research and scientific papers

Kinetic resolution of 2-substituted 2,3-dihydro-4-pyridones by palladium-catalyzed asymmetric allylic alkylation: Catalytic asymmetric total synthesis of indolizidine (-)-209I

The kinetic resolution of 2-substituted-2,3-dihydro-4-pyridones was realized via a Pd-catalyzed allylic substitution reaction using a commercially available (S)-P-Phos as a ligand, affording optically active dihydropyridones and C-allylated dihydropyridones in high yields and good enantioselectivities with the S-factor up to 43. With this protocol, a catalytic asymmetric total synthesis of indolizidine (-)-209I was realized for the first time.

Synthesis of 6- and 7-membered cyclic enaminones: Scope and mechanism

Six- and seven-membered cyclic enaminones can be prepared using common, environmentally benign reagents. Amino acids are used as synthetic precursors allowing diversification and the incorporation of chirality. The key reaction in this multistep process involves deprotection of Boc-amino ynones and subsequent treatment with methanolic K2CO3 to induce cyclization. A β-amino elimination side reaction was identified in a few labile substrates that led to either loss of stereochemical purity or degradation. This process can be mitigated in specific cases using mild deprotection conditions. NMR and deuterium-labeling experiments provided valuable insight into the workings and limitations of this reaction. Although disguised as a 6-endo-dig cyclization, the reagents employed in the transformation play a direct role in bond-making and bond-breaking, thus changing the mode of addition to a 6-endo-trig cyclization. This method can be used to construct an array of monocyclic and bicyclic scaffolds, many of which are found in well-known natural products (e.g., indolizidine, quinolizidine, and Stemona alkaloids).

Aza Diels-Alder reactions of sulfinimines with the Rawal diene

The aza Diels-Alder reaction of optically active sulfinimines with the Rawal diene leads to enantiomerically enriched dihydropyridones with ees up to 90%. The reaction was catalyzed by TMSOTf. The best results were obtained using 10-isobornylsulfinimines.