On the unexpected stereochemical outcome of the magnesium in methanol - Conjugate reduction of an exocyclic alpha,beta-unsaturated ester

Authors
Gabriels, S Van Haver, D Vandewalle, M De Clercq, P Viterbo, D
Citation
S. Gabriels et al., On the unexpected stereochemical outcome of the magnesium in methanol - Conjugate reduction of an exocyclic alpha,beta-unsaturated ester, EUR J ORG C, (8), 1999, pp. 1803-1809
Citations number
38
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X → ACNP
Issue
8
Year of publication
1999
Pages
1803 - 1809
Database
ISI
SICI code
1434-193X(199908):8<1803:OTUSOO>2.0.ZU;2-G
Abstract
The conjugate reduction of the exocyclic alpha,beta-unsaturated ester 9 wit h magnesium in methanol gives a mixture of diastereoisomers containing pred ominantly the less stable 10a. Eventual structural identification rests on the X-ray diffraction analysis of tosylate 18.