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.
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 efficient resolution of (+/-)- 7 has been achieved through enantioselective acetylation catalyzed by Candida antarctica lipase B. Straightforward and enantioselective syntheses of 4-hydroxy-2-cyclohexenone, 1, trans-cyclohex-2-ene-1,4-diol, 2, and their O-protected derivatives 18 and 19 have been readily accomplished from 7.
Bayón
Pau
P
Universitat Autònoma de Barcelona, Departament de Química, 08193 Bellaterra, Spain.
Marjanet
Georgina
G
Toribio
Gladis
G
Alibés
Ramon
R
de March
Pere
P
Figueredo
Marta
M
Font
Josep
J
D000107:Acetylation; D002176:Candida albicans / Q000201:enzymology; D002384:Catalysis; D003510:Cyclohexanes / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D003511:Cyclohexanols / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D003512:Cyclohexanones / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D008049:Lipase / Q000378:metabolism; D015394:Molecular Structure; D012995:Solubility; D013237:Stereoisomerism
C529503:4-hydroxy-2-cyclohexenone; D003510:Cyclohexanes; D003511:Cyclohexanols; D003512:Cyclohexanones; C529504:cyclohex-2-ene-1,4-diol; C506365:Cyclohexane; D008049:Lipase