2-Oxiranyl-pyridines: Synthesis and Regioselective Epoxide Ring Openings with Chiral Amines as a Route to Chiral Ligands

Autor:	Jacek Skarżewski, Marzena Wosińska-Hrydczuk
Rok vydání:	2019
Předmět:	Chiral auxiliary Article Subject Diastereomer Regioselectivity Epoxide General Chemistry Medicinal chemistry lcsh:QD146-197 Stereocenter lcsh:QD241-441 chemistry.chemical_compound lcsh:Organic chemistry chemistry Aldol reaction Styrene oxide Pyridine lcsh:Inorganic chemistry
Zdroj:	Heteroatom Chemistry, Vol 2019 (2019)
ISSN:	1098-1071 1042-7163
DOI:	10.1155/2019/2381208
Popis:	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.
Databáze:	OpenAIRE
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