Selective mono-N-alkylation of 3-amino alcohols via chelation to 9-BBN

Galia Bar-Haim, Moshe Kol

Research output: Contribution to journalArticlepeer-review

Abstract

(Chemical Equation Presented) 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.

Original languageEnglish
Pages (from-to)3549-3551
Number of pages3
JournalOrganic Letters
Volume6
Issue number20
DOIs
StatePublished - 30 Sep 2004

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