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 -