132658-89-0

Upstream product

• 132658-85-6 Acetic acid (7S,8R)-7-((R)-toluene-4-sulfinyl)-1,4-dioxa-spiro[4.5]dec-8-yl ester 
• 132617-15-3 (1R,4S)-4-hydroxycyclohex-2-en-1-yl acetate 
• 78776-45-1 cis-2-cyclohexenyl-1,4-diacetate 
• 1215294-99-7 C₁₇H₂₂O₇S 
• 77300-23-3 cyclohex-(±)-(1R*,4S*)-2-ene-1,4-diyl dibenzoate 
• 127-09-3 sodium acetate 
• 132658-84-5 (7S,8R)-7-((R)-Toluene-4-sulfinyl)-1,4-dioxa-spiro[4.5]decan-8-ol 
• 132658-83-4 (S)-7-((R)-Toluene-4-sulfinyl)-1,4-dioxa-spiro[4.5]decan-8-one 
• 4746-97-8 cyclohexanedione monoethylene ketal 
• 30182-12-8 4-hydroxy-2-cyclohexenone 
• 794526-36-6 Acetic acid (1R,2S)-2-benzylsulfanyl-4-oxo-cyclohexyl ester 

Downstream Products

• 132746-89-5 (+)-(R)-4-hydroxycyclohex-2-enone 

Relevant academic research and scientific papers

Asymmetric synthesis of chiral cycloalkenone derivatives via palladium catalysis

The palladium-catalyzed oxidative desymmetrization of meso-dibenzoates yields γ-benzoyloxy cycloalkenones in good yields and with excellent levels of enantioselectivity. These compounds serve as precursors to a broad range of substituted cycloalkenones, including well-established synthetic building blocks and elaborated cycloalkanone derivatives. The ability to prepare both enantiomers of the oxidative desymmetrization products enables a unified strategy toward stereochemically diverse epoxyquinoid natural products.

The thio-adduct facilitated, enzymatic kinetic resolution of 4-hydroxycyclopentenone and 4-hydroxycyclohexenone

The addition of 3,4-dimethoxybenzyl thiol 8, as a benzyl thiol surrogate, to racemic 4-hydroxycyclopent-2-enone 2 and 4-hydroxycyclohex-2-enone 15 gave the corresponding cis-adducts (±)-3-(3,4-dimethoxybenzylthio)-4- hydroxycyclopentanone 4b and (±)-3-(3,4-dimethoxybenzylthio)-4- hydroxycyclohexanone 16 with good diastereocontrol. In both cases, subsequent treatment with vinyl acetate, in the presence of a lipase enabled enantiomer resolution. Thus, (+)-16 and the acetate of its enantiomer, (-)-(1R,2S)-2-(3,4- dimethoxybenzylthio)-4-oxocyclohexyl acetate, (-)-17 were isolated in 98% enantiomeric excess. Based on the 1,4-dioxygenation pattern, (-)-17 can be used to prepare both enantiomers of 4-(tert-butyldimethylsilyloxy)cyclohex-2-enone 19. Firstly, saponification, with a sub-stoichiometric amount of NaOMe, followed by a one-pot silyl ether formation-sulfide elimination sequence gave (+)-19. Then using the same starting material a 6-step sequence, featuring a diastereoselective NaBH4 reduction and a Cope-type sulfoxide elimination, gave (-)-19.

Facile biocatalytic syntheses of optically active 4-hydroxycyclohex-2-enone and 4-benzylthiacyclopent-2-enone

Novozyme 435 (Candida antarctica Lipase B) effects the kinetic resolution of both 3-benzylthia-4-hydroxycyclopentanone and its six-membered ring analogue, providing a novel route to both enantiomers of 4-benzylthiacyclopent-2-enone and the two enantiomers of 4-hydroxycyclohex-2- enone, all in a state of very high optical purity.

ASYMMETRIC SYNTHESIS OF (R) AND (S)-4-HYDROXY-2-CYCLOHEXENONE AND DERIVATIVES

The asymmetric syntheses of both enantiomers of 4-hydroxy-2-cyclohexenone and their O-acyl and O-benzyl derivatives are reported.DIBAL and ZnCl2/DIBAL stereoselective reductions of the ketosulfoxides resulting in the sulfinylation of 1,4-cyclohexanedione