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Selective Mono-N-alkylation of 3-Amino Alcohols via Chelation to 9-BBN

Galia Bar-Haim and Moshe Kol*

*The School of Chemistry, Raymond and Beverly Sackler Faculty of Exact Sciences, Tel Aviv University, Ramat Aviv, Tel Aviv 69978, Israel, Email:

G. Bar-Haim, M. Kol, Org. Lett., 2004, 6, 3549-3551.

DOI: 10.1021/ol048554k


A selective mono-N-alkylation of 3-amino alcohols relies on formation of a stable chelate with 9-BBN. Three prototypical amino alcohols featuring various bridging units led selectively to the monoalkylated derivatives in very high yields.

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Key Words

N-Alkylation, Borane-Amine Adducts

ID: J54-Y2004-810