title: Selective mono-N-alkylation of 3-amino alcohols via chelation to 9-BBN.
abstract: [reaction: see text] A method for selective mono-N-alkylation of amino alcohols is introduced. This method relies on formation of a stable chelate with 9-BBN, which serves in the dual roles of protecting and activating the amine group. Three prototypical amino alcohols featuring various three-carbon bridging units led selectively to the monoalkylated derivatives in very high yields. The straightforward synthesis of the N-CD3 derivatives demonstrates the effectiveness of this approach.
authors.affiliation: The School of Chemistry, Raymond and Beverly Sackler Faculty of Exact Sciences, Tel Aviv University, Ramat Aviv, Tel Aviv 69978, Israel.
authors.forename: Galia
authors.initials: G
authors.lastname: Bar-Haim
authors.forename: Moshe
authors.initials: M
authors.lastname: Kol