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

Regis Tripoli; Tory N. Cayzer; Anthony C. Willis; Michael S. Sherburn; Michael N. Paddon-Row

doi:10.1039/b708324f

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

Regis Tripoli, Tory N. Cayzer, Anthony C. Willis^*, Michael S. Sherburn, Michael N. Paddon-Row

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

9 Citations (Scopus)

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.

Original language	English
Pages (from-to)	2606-2616
Number of pages	11
Journal	Organic and Biomolecular Chemistry
Volume	5
Issue number	16
DOIs	https://doi.org/10.1039/b708324f
Publication status	Published - 2007

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@article{8094c0d9f2a24dd1a239896e37fb2037,

title = "Stereocontrol of intramolecular Diels-Alder reactions by an allylic diphenylcyclopropyl group",

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 {\AA}), providing support to the notion that these reactions are concerted processes.",

author = "Regis Tripoli and Cayzer, \{Tory N.\} and Willis, \{Anthony C.\} and Sherburn, \{Michael S.\} and Paddon-Row, \{Michael N.\}",

year = "2007",

doi = "10.1039/b708324f",

language = "English",

volume = "5",

pages = "2606--2616",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "16",

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T1 - Stereocontrol of intramolecular Diels-Alder reactions by an allylic diphenylcyclopropyl group

AU - Tripoli, Regis

AU - Cayzer, Tory N.

AU - Willis, Anthony C.

AU - Sherburn, Michael S.

AU - Paddon-Row, Michael N.

PY - 2007

Y1 - 2007

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/34547563527

U2 - 10.1039/b708324f

DO - 10.1039/b708324f

M3 - Article

SN - 1477-0520

VL - 5

SP - 2606

EP - 2616

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 16

ER -

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

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