104323-66-2Relevant academic research and scientific papers
Alkylation and Oligomerization of the Lithium Enolate of 2-Norbornenones. Stereochemical Consequences of Enolate Aggregation
Horner, John H.,Vera, Marisol,Grutzner, John B.
, p. 4212 - 4220 (2007/10/02)
Alkylation of the lithium enolate of norbornenone in THF with alkyl halides gave a single trimeric oligomer containing one alkyl group as the major product.The structure of this diastereomer has been determined by 1H and 13 2-D NMR techniques and analysis of relaxation times.Direct reaction in the aggregated enolate with the Zimmerman-House-Jackman cubic structure is implied.Compounds with a 7-anti substituent could be alkylated in satisfactory yield.The use of the dimethylhydrazone anion as an enolate equivalent gave good yields of 3-alkylnorbornenones (methyl, n-hexyl, benzyl). 1H and 13C NMR data for products and intermediates are reported.
