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Allylic stereocontrol of the intramolecular Diels-Alder reaction

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Date

2005

Authors

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

Journal Title

Journal ISSN

Volume Title

Publisher

Wiley-VCH Verlag GMBH

Abstract

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.

Description

Keywords

Keywords: Addition reactions; Alcohols; Derivatives; Esters; Isomers; Mathematical models; Probability density function; Substitution reactions; Substrates; Synthesis (chemical); Chiral pool; Cycloaddition; Density functional calculations; Diastereoselectivity; Syn Chiral pool; Cyclo-addition; Density functional calculations; Diastereoselectivity; Synthetic methods

Citation

URI

http://hdl.handle.net/1885/76104

Collections

ANU Research Publications

Source

Chemistry, A European Journal

Type

Journal article

Book Title

Entity type

Access Statement

License Rights

DOI

10.1002/chem.200401215

Restricted until

2037-12-31

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01_Lilly_Allylic_stereocontrol_of_the_2005.pdf (263.74 KB)

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