124890-95-5Relevant academic research and scientific papers
Asymmetric Induction in the Wittig-Still Rearrangement of Ethers Containing an Allylic Stereocenter - Diastereocontrol by Allylic Oxygen
Priepke, Henning,Brueckner, Reinhard
, p. 153 - 168 (2007/10/02)
Stannylated allyl ethers 13, 15, 19 and 21 bearing an allylic center of chirality are submitted to the Still variant of the Wittig rearrangement.In these reactions alkoxy groups at the chiral center exert stereocontrol through asymmetric induction.With only few exceptions , the syn-configurated rearrangement product (27) is formed in preference to the anti epimer (28), syn:anti ratios are often >90:98:3J between β- and γ-protons may be used to assign the stereochemistry in epimeric syn and anti γ-alkoxy alcohols.
Stereoselective Intramolecular Nitrone Cycloadditions Promoted by an Allylic Stereocenter
Annunziata, Rita,Cinquini, Mauro,Cozzi, Franco,Raimondi, Laura
, p. 1901 - 1908 (2007/10/02)
A series of intramolecular nitrone cycloadditions to chiral allyl ethers was studied in order to evaluate the influence on the stereochemical outcome exerted by several factors, including the nature of the substituents at the stereocenter and the steric and electronic features of the double bond.A comparison between the stereoselectivity of these reactions and that of related nitrile oxides cycloadditions suggests that they could proceed via similar transition states.
