2-Oxiranyl-pyridines: Synthesis and Regioselective Epoxide Ring Openings with Chiral Amines as a Route to Chiral Ligands
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 chir...
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| Format: | Article |
| Language: | English |
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Wiley
2019-01-01
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| Series: | Heteroatom Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2019/2381208 |
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| author | Marzena Wosińska-Hrydczuk Jacek Skarżewski |
| author_facet | Marzena Wosińska-Hrydczuk Jacek Skarżewski |
| author_sort | Marzena Wosińska-Hrydczuk |
| collection | DOAJ |
| description | 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. |
| format | Article |
| id | doaj-art-5bea2b68838c41c0aadd6bb2a068358f |
| institution | Kabale University |
| issn | 1042-7163 1098-1071 |
| language | English |
| publishDate | 2019-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Heteroatom Chemistry |
| spelling | doaj-art-5bea2b68838c41c0aadd6bb2a068358f2025-02-03T06:11:32ZengWileyHeteroatom Chemistry1042-71631098-10712019-01-01201910.1155/2019/238120823812082-Oxiranyl-pyridines: Synthesis and Regioselective Epoxide Ring Openings with Chiral Amines as a Route to Chiral LigandsMarzena Wosińska-Hrydczuk0Jacek Skarżewski1Department of Organic Chemistry, Faculty of Chemistry, Wrocław University of Technology, Wyb Wyspiańskiego 27, 50-370 Wrocław, PolandDepartment of Organic Chemistry, Faculty of Chemistry, Wrocław University of Technology, Wyb Wyspiańskiego 27, 50-370 Wrocław, PolandNew 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.http://dx.doi.org/10.1155/2019/2381208 |
| spellingShingle | Marzena Wosińska-Hrydczuk Jacek Skarżewski 2-Oxiranyl-pyridines: Synthesis and Regioselective Epoxide Ring Openings with Chiral Amines as a Route to Chiral Ligands Heteroatom Chemistry |
| title | 2-Oxiranyl-pyridines: Synthesis and Regioselective Epoxide Ring Openings with Chiral Amines as a Route to Chiral Ligands |
| title_full | 2-Oxiranyl-pyridines: Synthesis and Regioselective Epoxide Ring Openings with Chiral Amines as a Route to Chiral Ligands |
| title_fullStr | 2-Oxiranyl-pyridines: Synthesis and Regioselective Epoxide Ring Openings with Chiral Amines as a Route to Chiral Ligands |
| title_full_unstemmed | 2-Oxiranyl-pyridines: Synthesis and Regioselective Epoxide Ring Openings with Chiral Amines as a Route to Chiral Ligands |
| title_short | 2-Oxiranyl-pyridines: Synthesis and Regioselective Epoxide Ring Openings with Chiral Amines as a Route to Chiral Ligands |
| title_sort | 2 oxiranyl pyridines synthesis and regioselective epoxide ring openings with chiral amines as a route to chiral ligands |
| url | http://dx.doi.org/10.1155/2019/2381208 |
| work_keys_str_mv | AT marzenawosinskahrydczuk 2oxiranylpyridinessynthesisandregioselectiveepoxideringopeningswithchiralaminesasaroutetochiralligands AT jacekskarzewski 2oxiranylpyridinessynthesisandregioselectiveepoxideringopeningswithchiralaminesasaroutetochiralligands |