Enantioselective Acylphosphonylation-Dual Lewis Acid-Lewis Base Activation of Aldehyde and Acylphosphonate
2014 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 79, no 13, 6172-6178 p.Article in journal (Refereed) Published
Acetoxyphosphonates were obtained by a one-step procedure consisting of reaction of diethyl acetylphosphonate with prochiral aldehydes in the presence of a catalytic system comprising a chiral Lewis acid, an achiral Lewis base, and a Bronstedt base. Best results were obtained using a tridentate Schiff base aluminum(III) Lewis acidic complex, 1H-1,2,3-benzotriazole, and a tertiary amine such as DBU. The target compounds were in most cases obtained in high yields, but with moderate enantiomeric ratios (up to 78:22).
Place, publisher, year, edition, pages
2014. Vol. 79, no 13, 6172-6178 p.
Aldehydes, Complexation, Functional groups, Acylphosphonate, Catalytic system, Chiral Lewis acid, Enantiomeric ratio, Enantioselective, Prochiral aldehydes, Target compound, Tridentate Schiff-base
IdentifiersURN: urn:nbn:se:kth:diva-148610DOI: 10.1021/jo500895uISI: 000338693300026ScopusID: 2-s2.0-84903717843OAI: oai:DiVA.org:kth-148610DiVA: diva2:737068
FunderWenner-Gren FoundationsSwedish Research Council, 621-2012-3391
QC 201408112014-08-112014-08-112015-09-08Bibliographically approved