Selective mono-N-alkylation of 3-amino alcohols via chelation to 9-BBN.
[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.
Bar-Haim
Galia
G
The School of Chemistry, Raymond and Beverly Sackler Faculty of Exact Sciences, Tel Aviv University, Ramat Aviv, Tel Aviv 69978, Israel.
Kol
Moshe
M