Density Functional Theory Study of the Cinchona Thiourea-Catalyzed Henry reaction: Mechanism and Enantioselectivity
2007 (English)In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 349, no 17-18, 2537-2548 p.Article in journal (Refereed) Published
We report a density functional theory investigation of the enantioselective Cinchona thiourea-catalyzed Henry reaction of aromatic aldehydes with nitromethane. We show that two pathways (differing in the binding modes of the reactants to the catalyst) are possible for the formation of the C-C bond, and that they have comparable reaction barriers. The enantioselectivity is investigated, and our results are in agreement with the experimentally observed solvent dependence of the reaction.
Place, publisher, year, edition, pages
2007. Vol. 349, no 17-18, 2537-2548 p.
cinchona alkaloids, density functional theory, enantioselectivity, nitroaldol reaction, organocatalysis
IdentifiersURN: urn:nbn:se:kth:diva-8243DOI: 10.1002/adsc.200700367ISI: 000251737500003ScopusID: 2-s2.0-37349098707OAI: oai:DiVA.org:kth-8243DiVA: diva2:13512
QC 201007192008-04-222008-04-222010-11-11Bibliographically approved