853953-48-7Relevant academic research and scientific papers
Allylic stereocontrol of the intramolecular diels-alder reaction
Lilly, Michael J.,Miller, Natalie A.,Edwards, Alison J.,Willis, Anthony C.,Turner, Peter,Paddon-Row, Michael N.,Sherburn, Michael S.
, p. 2525 - 2536 (2005)
The stereochemical outcome of the intramolecular Diels-Alder reaction of ester-linked 1,3,8-nonatrienes can be controlled by substituants about a stereogenic center attached to Cl. The scope and limitations of this approach have been investigated, with variation in substrate structure about the allylic stereocenter and the dieno phile. The stereochemical outcomes of these reactions are explained by reference to B3LYP/6-31G(d) transition structures. New insights into the conformational preferences of allylic alcohol derivatives are reported, results which allow an explanation of the differing levels of π-diastereofacial selectivity and cis/trans (i.e. endo/exo) selectivity from the reaction.
