2-Oxiranyl-pyridines: Synthesis and Regioselective Epoxide Ring Openings with Chiral Amines as a Route to Chiral Ligands
Joint Authors
Wosińska-Hrydczuk, Marzena
Skarżewski, Jacek
Source
Issue
Vol. 2019, Issue 2019 (31 Dec. 2019), pp.1-12, 12 p.
Publisher
Hindawi Publishing Corporation
Publication Date
2019-10-09
Country of Publication
Egypt
No. of Pages
12
Main Subjects
Abstract EN
New epoxides, derivatives of pyridine, 2,2′-bipyridine, and 1,10-phenanthroline, were synthesized from the respective α-methylazaarenes.
The obtained racemic 2-oxiranyl-azaarenes along with styrene oxide and trans-stilbene oxide were submitted to the ring opening with chiral primary amines as a chiral auxiliary.
The most effective reaction was run in the presence of Sc(OTf)3/diisopropylethylamine for 7 days at 80°C, affording a good yield of the amino alcohols.
Except for styrene oxide which gave both α- and β-amino alcohols, the reactions led regioselectively to the corresponding diastereomeric β-amino alcohols.
The resulting diastereomers were separated, and the configurations of their stereogenic centers were established.
The obtained enantiomerically pure 2-pyridinyl- and 6-(2,2′-bipyridinyl)-β-amino alcohols were tentatively tested as chiral ligands in the zinc-catalyzed aldol reaction.
American Psychological Association (APA)
Wosińska-Hrydczuk, Marzena& Skarżewski, Jacek. 2019. 2-Oxiranyl-pyridines: Synthesis and Regioselective Epoxide Ring Openings with Chiral Amines as a Route to Chiral Ligands. Heteroatom Chemistry،Vol. 2019, no. 2019, pp.1-12.
https://search.emarefa.net/detail/BIM-1155634
Modern Language Association (MLA)
Wosińska-Hrydczuk, Marzena& Skarżewski, Jacek. 2-Oxiranyl-pyridines: Synthesis and Regioselective Epoxide Ring Openings with Chiral Amines as a Route to Chiral Ligands. Heteroatom Chemistry No. 2019 (2019), pp.1-12.
https://search.emarefa.net/detail/BIM-1155634
American Medical Association (AMA)
Wosińska-Hrydczuk, Marzena& Skarżewski, Jacek. 2-Oxiranyl-pyridines: Synthesis and Regioselective Epoxide Ring Openings with Chiral Amines as a Route to Chiral Ligands. Heteroatom Chemistry. 2019. Vol. 2019, no. 2019, pp.1-12.
https://search.emarefa.net/detail/BIM-1155634
Data Type
Journal Articles
Language
English
Notes
Includes bibliographical references
Record ID
BIM-1155634