169331-39-9

Upstream product

• 116950-01-7 (2S,3S,8aR)-Hexahydro-3-(hydroxymethyl)-8a-methyl-2-phenyl-5-oxo-5H-oxazolo<3,2-a>pyridine 
• 191805-34-2 (2S,3S,8aR)-5-Ethylsulfanyl-3-methoxymethyl-8a-methyl-2-phenyl-2,3,8,8a-tetrahydro-7H-oxazolo[3,2-a]pyridine 
• 191805-36-4 (2S,3S,8aR)-3-Methoxymethyl-8a-methyl-2-phenyl-2,3,8,8a-tetrahydro-7H-oxazolo[3,2-a]pyridine-5-carbonitrile 
• 191805-58-0 (2S,3S,7S,8aR)-7-Benzyl-3-methoxymethyl-8a-methyl-2-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-one 
• 85450-51-7 (±)-3-benzylcyclohexanone 
• 1026043-64-0 (2S,3S,7S,8aR)-7-Benzyl-3-methoxymethyl-8a-methyl-2-phenyl-2,3,8,8a-tetrahydro-7H-oxazolo[3,2-a]pyridine-5-carbonitrile 
• 191805-32-0 (2S,3S,8aR)-3-Methoxymethyl-8a-methyl-2-phenyl-hexahydro-oxazolo[3,2-a]pyridine-5-thione 
• 155395-70-3 (2S,3S,8aR)-3-Methoxymethyl-8a-methyl-2-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-one 

Relevant academic research and scientific papers

Asymmetric Baeyer-Villiger oxidation: Classical and parallel kinetic resolution of 3-substituted cyclohexanones and desymmetrization of: Meso -disubstituted cycloketones

Regioselectivity is a crucial issue in Baeyer-Villiger (BV) oxidation. To date, few reports have addressed asymmetric BV oxidation of 3-substituted cycloketones due to the high difficulty of controlling regio- and stereoselectivity. Herein, we report the asymmetric BV oxidation of 3-substituted and meso-disubstituted cycloketones with chiral N,N′-dioxide/Sc(iii) catalysts performed in three ways: classical kinetic resolution, parallel kinetic resolution and desymmetrization. The methodology was applied in the total and formal synthesis of bioactive compounds and natural products. Control experiments and calculations demonstrated that flexible and adjustable catalysts played a significant role in the chiral recognition of substrates.

Chiral bicyclic lactams as homoenolate equivalents: An asymmetric route to 5-substituted cyclohexenones

Bicyclic Lactam 2 was transformed info α-cyanoenamine 8 in a four- step, high-yielding process. γ-Metalation of 8 was achieved using LiTMP in THF/HMPA, and the resultant homoenolate equivalent underwent stereoselective alkylation and subsequent hydrolysis to provide lactams of type 10 as a single diasteraomer. Partial reduction and hydrolysis of lactams 10 furnished enantiopure 5-substituted cyclohexenones 13 in good overall yield.