127716-85-2Relevant academic research and scientific papers
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 (1990)
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.
Regio- and stereospecific synthesis of substituted cyclohexenediols from 7-oxabicyclo[2.2.1]hept-5-en-2-ols and organolithium reagents
Arjona,Fernandez de la Pradilla,Garcia,Martin-Domenech,Plumet
, p. 6437 - 6440 (2007/10/02)
The bridge opening reactions of 7-oxabicyclo[2.2.1]hept-5-en-2-ols, 4 and 6 with organolithium reagents proceed with complete regio- and stereoselectivity to produce highly functionalized cyclohexene derivatives 5 and 7, respectively.
