99300-05-7Relevant academic research and scientific papers
The addition of electophiles on ester enolates containing an oxygen in the β-position. A stereoelctronically controlled reaction
Caron, Maurice,Kawamata, Takeshi,Ruest, Luc,Soucy, Pierre,Deslongchamps, Pierre
, p. 1781 - 1787 (2007/10/02)
The enolate anion derived from spiro ketal methyl esters (1,3, and 4) reacts with various electrophiles (PhSeBr, CH3I, O2, I2, (CH3S)2, and (PhS)2 to yield as the major product, the isomer resulting from an equatorial approach of the electrophilic reagent.This stereochemically controlled reaction is discusseed in terms of stereoelectronic effects that increase the electron density of the α face of the enolate anion.
