Synthesis 2017; 49(06): 1231-1242
DOI: 10.1055/s-0036-1588356
paper
© Georg Thieme Verlag Stuttgart · New York

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

Joseph R. Lizza
Chemistry and Biochemistry Department, Rowan University, Glassboro, NJ 08028, USA   Email: [email protected]
,
Gustavo Moura-Letts*
Chemistry and Biochemistry Department, Rowan University, Glassboro, NJ 08028, USA   Email: [email protected]
› Author Affiliations
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.

Supporting Information

 
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