102648-76-0Relevant academic research and scientific papers
Direct Asymmetric Synthesis of Quaternary Carbon Centers via Addition-Elimination Process: Nitroolefination of α-Substituted δ-Lactones
Fuji, Kaoru,Node, Manabu,Nagasawa, Hideko,Naniwa, Yoshimitsu,Taga, Tooru,et al.
, p. 7921 - 7925 (1989)
The reactions of chiral nitro enamines 2a-c with zinc enolates 4-6 of α-substituted δ-lactones afforded α,α-disubstituted δ-lactones with a high ee through an addition-elimination process.The best results were obtained with the reaction of 2c with 5.Michael-type addition of the enolate onto the nitro enamine is kinetically controlled and decides the absolute stereochemistry of the product.A cyclic transition model is proposed to rationalize the S-selectivity.
