Solvent-Directed Epoxide Opening with Primary Amines for the Synthesis of β-Amino Alcohols

Joseph R. Lizza; Gustavo Moura-Letts

doi:10.1055/s-0036-1588356

Synthesis, Table of Contents

Synthesis 2017; 49(06): 1231-1242
DOI: 10.1055/s-0036-1588356

paper

Solvent-Directed Epoxide Opening with Primary Amines for the Synthesis of β-Amino Alcohols

Authors

Joseph R. Lizza

Chemistry and Biochemistry Department, Rowan University, Glassboro, NJ 08028, USA Email: moura-letts@rowan.edu
Gustavo Moura-Letts*

Chemistry and Biochemistry Department, Rowan University, Glassboro, NJ 08028, USA Email: moura-letts@rowan.edu

Abstract

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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-blockers

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References

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