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Allylic stereocontrol of the intramolecular Diels-Alder reaction

Lilly, Michael; Miller, Natalie; Edwards, Alison; Willis, Anthony; Turner, Peter; Paddon-Row, Michael; Sherburn, Michael

Description

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...[Show more]

CollectionsANU Research Publications
Date published: 2005
Type: Journal article
URI: http://hdl.handle.net/1885/76104
Source: Chemistry, A European Journal
DOI: 10.1002/chem.200401215

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