942514-50-3Relevant articles and documents
An efficient protocol for the enantioselective preparation of a key polyfunctionalized cyclohexane. New access to (R)- and (S)-4-hydroxy-2- cyclohexenone and (R)- and (S)-trans-cyclohex-2-ene-1,4-diol
Bayon, Pau,Marjanet, Georgina,Toribio, Gladis,Alibes, Ramon,De March, Pere,Figueredo, Marta,Font, Josep
, p. 3486 - 3491 (2008)
(Chemical Equation Presented) Starting from very accessible raw materials such as p-methoxyphenol, ethylene glycol, and thiophenol, a protocol has been developed to prepare multigram quantities of the polyfunctionalized cyclohexane (±)-7. A highly efficie
The thio-adduct facilitated, enzymatic kinetic resolution of 4-hydroxycyclopentenone and 4-hydroxycyclohexenone
O'Byrne, Aisling,Murray, Cian,Keegan, Dearbhla,Palacio, Carole,Evans, Paul,Morgan, Ben S.
supporting information; experimental part, p. 539 - 545 (2010/05/11)
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.
