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

Galia Bar-Haim; Moshe Kol

doi:10.1021/ol048554k

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

Galia Bar-Haim, Moshe Kol^*

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article › peer-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 language	English
Pages (from-to)	3549-3551
Number of pages	3
Journal	Organic Letters
Volume	6
Issue number	20
DOIs	https://doi.org/10.1021/ol048554k
State	Published - 30 Sep 2004

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title = "Selective mono-N-alkylation of 3-amino alcohols via chelation to 9-BBN",

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.",

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N2 - (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.

AB - (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.

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

Abstract

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