97997-19-8Relevant academic research and scientific papers
Nucleophilic substitution gone awry: A novel cyclopropanation reaction with a surprising stereochemical outcome
Torborg, Charles J.,Rabasco, John J.,Kass, Steven R.
, p. 6025 - 6028 (2007/10/02)
Lithium triethylborohydride reacts with the triisopropylbenzene sulfonate ester of 2-methoxy-5,5-dimethyl-2-vinyl-3-cyclohexen-1-ol (1) to afford 8-methoxy-6,6-dimethylspiro[2.5]oct-4-ene (3). Labeling studies reveal that this novel cyclopropane forming reaction proceeds with retention of configuration at the newly formed quaternary center.
A General Method for the Preparation of γ-Substituted Cyclohexenals and Cycloheptenals
Jones, Tood K.,Denmark, Scott E.
, p. 4037 - 4045 (2007/10/02)
A general procedure for the preparation of γ-substituted or β'-unsaturated cycloalkenals is described.Starting from 2-cycloalkenones substituents may be introduced as nucleophiles by 1,4-addition followed by trapping of the regiospecifically generated enolate (86-92percent).Peracid oxidation of the enol silane derivative produces an α-hydroxy ketone which, after protection (70-93percent), is homologated to an enol ether by a Horner-Wittig reaction.Mild hydrolysis of the labile vinylogous acetal produces the aldehydes in good yields (62-75percent).Advantages of this method in comparison to known procedures are discussed as are other unsuccessful approaches to this substitution pattern.
