Tetrahedron p. 8187 - 8198 (1990)
Update date:2022-08-05
Topics:
Arjona, Odon
Pradilla, Roberto Fernandez de la
Martin-Domenech, Angel
Plumet, Joaquin
The nucleophilic SN2' bridge opening of 7-oxabicyclo<2.2.1>hept-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.
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