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Stereocontrol of intramolecular Diels-Alder reactions by an allylic diphenylcyclopropyl group

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Date

2007

Authors

Tripoli, Regis
Cayzer, Tory
Willis, Anthony
Sherburn, Michael
Paddon-Row, Michael

Journal Title

Journal ISSN

Volume Title

Publisher

Royal Society of Chemistry

Abstract

Intramolecular Diels-Alder reactions of ester-linked 1,3,8-nonatrienes carrying a diphenylcyclopropyl substituent attached to C1 proceed with high levels of stereoselectivity. The stereochemical outcomes of these reactions are explained by reference to B3LYP/6-31G(d) transition structures. Experimentally, the diphenylcyclopropane rings remain intact through these IMDA reactions, notwithstanding their predicted extremely high degree of asynchronicity (the B3LYP-computed lengths in the IMDA transition structures differ by as much as 1.1 Å), providing support to the notion that these reactions are concerted processes.

Description

Keywords

Keywords: Allylic diphenylcyclopropyl group; Degree of asynchronicity; Transition structures; Electron transitions; Functional groups; Molecular interactions; Reaction kinetics; Stereoselectivity; Esters; allyl compound; carboxylic acid; cyclopropane derivative; di

Citation

URI

http://hdl.handle.net/1885/29524

Collections

Open Access Research

Source

Organic and Biomolecular Chemistry

Type

Journal article

Book Title

Entity type

Access Statement

License Rights

DOI

10.1039/b708324f

Restricted until

2037-12-31

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01_Tripoli_Stereocontrol_of_2007.pdf (322.33 KB)

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