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

Martin G. Banwell; Cai Chun; Alison J. Edwards; Markus M. Vögtle

doi:10.1071/CH03112

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

Martin G. Banwell, Cai Chun, Alison J. Edwards, Markus M. Vögtle

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

13 Citations (Scopus)

Abstract

bis-Crotonate and related alpha;,β-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
Number of pages	9
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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Banwell, M. G., Chun, C., Edwards, A. J., & Vögtle, M. M. (2003). Competitive intramolecular Diels-Alder reactions of bis-α,β-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, 56(9), 861-869. https://doi.org/10.1071/CH03112

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title = "Competitive intramolecular Diels-Alder reactions of bis-α,β-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;,β-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 = "Banwell, {Martin G.} and Cai Chun and Edwards, {Alison J.} and V{\"o}gtle, {Markus M.}",

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, MG, Chun, C, Edwards, AJ & Vögtle, MM 2003, 'Competitive intramolecular Diels-Alder reactions of bis-α,β-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-α,β-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 G.; Chun, Cai; Edwards, Alison J. et al.
In: Australian Journal of Chemistry, Vol. 56, No. 9, 2003, p. 861-869.

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

TY - JOUR

T1 - Competitive intramolecular Diels-Alder reactions of bis-α,β-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 G.

AU - Chun, Cai

AU - Edwards, Alison J.

AU - Vögtle, Markus M.

PY - 2003

Y1 - 2003

N2 - bis-Crotonate and related alpha;,β-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;,β-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.

UR - http://www.scopus.com/inward/record.url?scp=0042281892&partnerID=8YFLogxK

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 -

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

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