71837-46-2Relevant academic research and scientific papers
An alternative procedure for the O-trimethylsilylation of enolates generated by copper-catalyzed 1,4-additions
Andringa,Oosterveld,Brandsma
, p. 1393 - 1396 (2007/10/02)
Anhydrous lithium bromide has been successfully used as an additive instead of hexamethylphosphoric triamide in the O-trimethylsilation of enolates generated by copper halide-catalyzed reaction of Grignard reagents with a number of α,β-unsaturated carbony
The vinylogous anomeric effect in 3-alkyl-2-chlorocyclohexanone oximes and oxime ethers
Denmark,Dappen,Sear,Jacobs
, p. 3466 - 3474 (2007/10/02)
A series of trans-3-alkyl-2-chlorocyclohexanones, 2(methyl, ethyl, isopropyl, and tert-butyl), have been prepared and shown to exist predominantly in the diequatorial chair conformation except the tert-butyl derivative which prefers a twist-boat. Formatio
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.
