Addition of Azomethine Ylides to Aldehydes: Mechanistic Dichotomy of Differentially Substituted alpha-Imino Esters
2010 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 20, 3927-3933 p.Article in journal (Refereed) Published
The formal 1,3-dipolar cycloaddition of azomethine ylides and aldehydes is explored, as hydrolysis of the resulting oxazolidine product gives facile access to valuable syn-beta-aryl-beta-hydroxy-alpha-amino esters. The use of using benzaldehyde-derived imines as the ylide precursor results in 1,3-dipolar cycloaddition with high conversions but low diastereoselectivity. In contrast, the employment of benzophenone-derived imines as the ylide precursor results in an aldol reaction, which gives the intermediate oxazolidine in high diastereoselectivity and requires a weak acid catalyst to achieve higher conversions.
Place, publisher, year, edition, pages
2010. no 20, 3927-3933 p.
Amino alcohols, Azomethine ylides, Aldol reaction, Cycloaddition
IdentifiersURN: urn:nbn:se:kth:diva-29445DOI: 10.1002/ejoc.201000377ISI: 000280428700019ScopusID: 2-s2.0-77954263292OAI: oai:DiVA.org:kth-29445DiVA: diva2:397050
FunderKnut and Alice Wallenberg FoundationSwedish Research Council
QC 201102112011-02-112011-02-022012-06-05Bibliographically approved