Competitive intramolecular Diels-Alder reactions of bis-a,ß-unsaturated ester derivatives of enzymatically derived and enantiopure cis-1,2-dihydrocatechols. Enantiodivergent synthesis of monochiral bicyclo[2.2.2]oct-2-enes

Martin Banwell; Chonhoon Chun; Alison Edwards; Markus Vogtle

doi:10.1071/CH03112

Competitive intramolecular Diels-Alder reactions of bis-a,ß-unsaturated ester derivatives of enzymatically derived and enantiopure cis-1,2-dihydrocatechols. Enantiodivergent synthesis of monochiral bicyclo[2.2.2]oct-2-enes

Martin Banwell, Chonhoon Chun, Alison Edwards, Markus Vogtle

Research output: Contribution to journal › Article

Abstract

bis-Crotonate and related alpha;,?-unsaturated ester derivatives of readily available and enantiomerically pure cis-1,2-dihydrocatechols engage, upon heating in refluxing toluene, in two competitive intramolecular Diels-Alder reactions to give varying mixtures of chromatographically separable and pseudo-enantiomeric bicyclo[2.2.2]oct-2-enes. Such adducts, many of which have been characterized by single-crystal X-ray analysis, are likely to serve as useful building blocks in natural products synthesis.

Original language	English
Pages (from-to)	861-869
Journal	Australian Journal of Chemistry
Volume	56
Issue number	9
DOIs	https://doi.org/10.1071/CH03112
Publication status	Published - 2003

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10.1071/CH03112

http://hdl.handle.net/1885/85806

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@article{6aca30fe7e894b85a33a616e8f0641d6,

title = "Competitive intramolecular Diels-Alder reactions of bis-a,{\ss}-unsaturated ester derivatives of enzymatically derived and enantiopure cis-1,2-dihydrocatechols. Enantiodivergent synthesis of monochiral bicyclo[2.2.2]oct-2-enes",

abstract = "bis-Crotonate and related alpha;,?-unsaturated ester derivatives of readily available and enantiomerically pure cis-1,2-dihydrocatechols engage, upon heating in refluxing toluene, in two competitive intramolecular Diels-Alder reactions to give varying mixtures of chromatographically separable and pseudo-enantiomeric bicyclo[2.2.2]oct-2-enes. Such adducts, many of which have been characterized by single-crystal X-ray analysis, are likely to serve as useful building blocks in natural products synthesis.",

author = "Martin Banwell and Chonhoon Chun and Alison Edwards and Markus Vogtle",

year = "2003",

doi = "10.1071/CH03112",

language = "English",

volume = "56",

pages = "861--869",

journal = "Australian Journal of Chemistry",

issn = "0004-9425",

publisher = "CSIRO",

number = "9",

}

Banwell, M, Chun, C, Edwards, A & Vogtle, M 2003, 'Competitive intramolecular Diels-Alder reactions of bis-a,ß-unsaturated ester derivatives of enzymatically derived and enantiopure cis-1,2-dihydrocatechols. Enantiodivergent synthesis of monochiral bicyclo[2.2.2]oct-2-enes', Australian Journal of Chemistry, vol. 56, no. 9, pp. 861-869. https://doi.org/10.1071/CH03112

Competitive intramolecular Diels-Alder reactions of bis-a,ß-unsaturated ester derivatives of enzymatically derived and enantiopure cis-1,2-dihydrocatechols. Enantiodivergent synthesis of monochiral bicyclo[2.2.2]oct-2-enes. / Banwell, Martin; Chun, Chonhoon; Edwards, Alison et al.
In: Australian Journal of Chemistry, Vol. 56, No. 9, 2003, p. 861-869.

Research output: Contribution to journal › Article

TY - JOUR

T1 - Competitive intramolecular Diels-Alder reactions of bis-a,ß-unsaturated ester derivatives of enzymatically derived and enantiopure cis-1,2-dihydrocatechols. Enantiodivergent synthesis of monochiral bicyclo[2.2.2]oct-2-enes

AU - Banwell, Martin

AU - Chun, Chonhoon

AU - Edwards, Alison

AU - Vogtle, Markus

PY - 2003

Y1 - 2003

N2 - bis-Crotonate and related alpha;,?-unsaturated ester derivatives of readily available and enantiomerically pure cis-1,2-dihydrocatechols engage, upon heating in refluxing toluene, in two competitive intramolecular Diels-Alder reactions to give varying mixtures of chromatographically separable and pseudo-enantiomeric bicyclo[2.2.2]oct-2-enes. Such adducts, many of which have been characterized by single-crystal X-ray analysis, are likely to serve as useful building blocks in natural products synthesis.

AB - bis-Crotonate and related alpha;,?-unsaturated ester derivatives of readily available and enantiomerically pure cis-1,2-dihydrocatechols engage, upon heating in refluxing toluene, in two competitive intramolecular Diels-Alder reactions to give varying mixtures of chromatographically separable and pseudo-enantiomeric bicyclo[2.2.2]oct-2-enes. Such adducts, many of which have been characterized by single-crystal X-ray analysis, are likely to serve as useful building blocks in natural products synthesis.

U2 - 10.1071/CH03112

DO - 10.1071/CH03112

M3 - Article

SN - 0004-9425

VL - 56

SP - 861

EP - 869

JO - Australian Journal of Chemistry

JF - Australian Journal of Chemistry

IS - 9

ER -