title: Highly enantioselective asymmetric direct aldol reaction promoted by aziridine amides constructed on chiral terpene scaffold.
abstract: Optically pure, diastereomeric aziridine amides built on the chiral skeletons of camphor, fenchone, and menthone have proven to be highly efficient ligands for enantioselective asymmetric direct aldol reaction in the presence of water and zinc triflate. Desired products were formed in moderate to high chemical yields (up to 95%) and with enantiomeric excess up to 99%. The influence of the stereogenic centers located at the aziridine subunit on the stereochemical course of the reaction is discussed.
authors.affiliation: Department of Organic and Applied Chemistry, University of Łódź, Łódź, Poland.
authors.forename: Zuzanna
authors.initials: Z
authors.lastname: Wujkowska
authors.affiliation: Department of Organic and Applied Chemistry, University of Łódź, Łódź, Poland.
authors.forename: Aleksandra
authors.initials: A
authors.lastname: Strojewska
authors.affiliation: Department of Organic and Applied Chemistry, University of Łódź, Łódź, Poland.
authors.forename: Adam M
authors.initials: AM
authors.lastname: Pieczonka
authors.affiliation: Department of Organic and Applied Chemistry, University of Łódź, Łódź, Poland.
authors.forename: Stanisław
authors.initials: S
authors.lastname: Leśniak
authors.affiliation: Department of Organic and Applied Chemistry, University of Łódź, Łódź, Poland.
authors.forename: Michał
authors.identifier: http://orcid.org/0000-0003-4803-8078
authors.initials: M
authors.lastname: Rachwalski
mesh_terms: D000577:Amides / Q000737:chemistry*; D001388:Aziridines / Q000737:chemistry*; D002384:Catalysis; D013237:Stereoisomerism; D013729:Terpenes / Q000737:chemistry*
chemical_list: D000577:Amides; D001388:Aziridines; D013729:Terpenes; C033132:aziridine
keywords: aldol reaction; amides; asymmetric synthesis; aziridines; chiral ligands