139760-52-4Relevant academic research and scientific papers
Diastereoselective ester enolate alkylations. Asymmetric syntheses of 3-alkyl-3-carbomethoxy-2-exo-methylenecyclohex-5-en-1-ones
Schultz, Arthur G.,Taylor, Richard E.
, p. 3937 - 3943 (2007/10/02)
Enolate 12, designed to take advantage of potential chelation sites on the chiral auxiliary, (S)-2-(methoxymethyl)pyrrolidine, gives excellent diastereoselectivities for alkyl-, propargyl-, and cyanomethylations; negligible diastereoselectivities were observed for allyl- and benzylations. The resulting 3-substituted 3-carbomethoxy-1,4-cyclohexadienes 3a-g were converted to 3-substituted 3-carbomethoxy-2-exo-methylenecyclohex-5-en-1-ones 4a-g. Experiments designed to detect the possible involvement of single-electron transfer during alkylation of enolate 12 indicate that alkylations most probably occur via the SN2 pathway.
