Organocatalytic asymmetric cross-aldol reaction of 2-chloroethoxy acetaldehyde: diversity-oriented synthesis of chiral substituted 1,4-dioxanes and morpholines
2013 (English)In: Tetrahedron: asymmetry, ISSN 0957-4166, E-ISSN 1362-511X, Vol. 24, no 2-3, 134-141 p.Article in journal (Refereed) Published
Herein we report a facile organocatalytic asymmetric direct cross-aldol reaction of 2-chloroethoxy acetaldehyde with aromatic aldehydes using (S)-(-)-alpha,alpha-diphenyl-2-pyrrolidinemethanol as an organocatalyst to afford anti-2-(2-chloroethoxy)-1-arylpropane-1,3-diols with excellent enantioselectivities (95-98%) and moderate diastereoselectivities (3.5-7:1). The 1,3-diols, obtained after the aldehyde reduction, represent highly functional intermediates that allow for further diversification into both chiral 1,4-dioxanes and morpholines, compounds that frequently display interesting biological activities.
Place, publisher, year, edition, pages
2013. Vol. 24, no 2-3, 134-141 p.
IdentifiersURN: urn:nbn:se:uu:diva-197659DOI: 10.1016/j.tetasy.2012.12.004ISI: 000315550900007OAI: oai:DiVA.org:uu-197659DiVA: diva2:613888