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Synthesis 2017; 49(06): 1231-1242
DOI: 10.1055/s-0036-1588356
DOI: 10.1055/s-0036-1588356
paper
Solvent-Directed Epoxide Opening with Primary Amines for the Synthesis of β-Amino Alcohols
Further Information
Publication History
Received: 02 October 2016
Accepted after revision: 27 October 2016
Publication Date:
29 November 2016 (online)
Abstract
An efficient synthesis of β-amino alcohols from a variety of epoxides and primary unbranched amines in the absence of any catalyst in high yields and regioselectivities is reported. A variety of polar mixed solvent systems allow for the selective formation of secondary amino alcohols over tertiary amino alcohols. The reaction scope extends to a wide variety of aromatic and aliphatic substituted epoxides and primary amines bearing complex functionality.
Key words
β-amino alcohols - primary amines - epoxide opening reactions - solvent-directed reactions - β-blockersSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588356. Copies of all 1H and 13C NMR spectra are included.
- Supporting Information
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