Asymmetric photodeconjugation of ammonium ene-carboxylates: temperature effects and evidence for the alpha-carbon of the dienolic species as a latenttrigonal centre

Authors
Henin, F Letinois, S Muzart, J
Citation
F. Henin et al., Asymmetric photodeconjugation of ammonium ene-carboxylates: temperature effects and evidence for the alpha-carbon of the dienolic species as a latenttrigonal centre, TETRAHEDR-A, 11(9), 2000, pp. 2037-2044
Citations number
43
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
11
Issue
9
Year of publication
2000
Pages
2037 - 2044
Database
ISI
SICI code
0957-4166(20000519)11:9<2037:APOAET>2.0.ZU;2-I
Abstract
The diastereoselective photodeconjugation of CH2Cl2 solutions of enantiopur e ammonium ene-carboxylates was studied and the results compared with those of the enantioselective photodeconjugation of ene-esters in the presence o f catalytic amounts of chiral aminoalcohols. We have observed a significant entropic effect and shown that a C-beta control of the selectivity is oper ative in the asymmetric protonation of the photodienolic species, (C) 2000 Elsevier Science Ltd. All rights reserved.