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.
STEREOSELECTIVE INTRAMOLECULAR NITRONE CYCLOADDITIONS PROMOTED BY AN ALLYLIC STEREOCENTER / R. ANNUNZIATA, M. CINQUINI, F. COZZI, L. RAIMONDI. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 55:6(1990), pp. 1901-1908.
STEREOSELECTIVE INTRAMOLECULAR NITRONE CYCLOADDITIONS PROMOTED BY AN ALLYLIC STEREOCENTER
R. ANNUNZIATAPrimo
;M. CINQUINISecondo
;F. COZZIPenultimo
;L. RAIMONDIUltimo
1990
Abstract
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.
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