133147-34-9Relevant articles and documents
RING-OPENING SN2' REACTIONS OF 7-OXANORBORNENES BY ORGANOLITHIUM REAGENTS. REGIO- AND STEREOSPECIFIC SYNTHESIS OF SUBSTITUTED CYCLOHEXENEDIOLS
Arjona, Odon,Pradilla, Roberto Fernandez de la,Martin-Domenech, Angel,Plumet, Joaquin
, p. 8187 - 8198 (2007/10/02)
The nucleophilic SN2' bridge opening of 7-oxabicyclohept-5-en-2-ols with organolithium reagents occurs in a regio- and stereospecific fashion to produce 6-substituted-cyclohex-4-en-1,3-diols, regardless of the stereochemistry at C-2.A free alcohol functionality is necessary to attain complete regiocontrol of the process.The methodology is utilized to prepare an optically pure cyclohexene derivative, (+)-(1S,3S,6R)-6-n-butyl-3-methyl-cyclohex-4-en-1,3-diol (5b), as a model system.