title: Diastereoselective synthesis of propargylic N-hydroxylamines via NHC-copper(I) halide-catalyzed reaction of terminal alkynes with chiral nitrones on water.
abstract: The first NHC-copper(I)-halide catalyzed addition of terminal alkynes to enantiomerically pure nitrones on water is described. This reaction provides a straightforward access to propargylic N-hydroxylamines in excellent yield and with excellent stereoselectivity (up to 97%). The presented methodology was applied as a key step in the formal synthesis of (-)-lentiginosine.
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland. michal.michalak@icho.edu.pl.
authors.forename: Ł
authors.initials: Ł
authors.lastname: Woźniak
authors.forename: O
authors.initials: O
authors.lastname: Staszewska-Krajewska
authors.forename: M
authors.initials: M
authors.lastname: Michalak