Opening of Diaryl Epoxides: ortho-Fluorophenyl and 2-Pyridyl Epoxides

Solladié‐Cavallo, Arlette; Lupattelli, Paolo; Marsol, C.; Isarno, Thomas; Bonini, Carlo; Caruso, Leonilde; Maiorella, Angelica

doi:10.1002/1099-0690(200204)2002:8<1439::aid-ejoc1439>3.3.co;2-s

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“…It should be noted that the epoxide 11 has already been opened in the MgBr 2 -supported reaction with the same regioselectivity. at result was explained by similar Mg 2+ complexation [52].…”

Section: Selective Epoxide Ring Opening: Pyridine Derivativesmentioning

confidence: 70%

“…Moreover, when cyclohexyl carbaldehyde was used in the reaction with 3, along with 6b the diene 7 was obtained. us, in the next step, 4, 5, and 6 were reacted with NBS in dioxane/water acidified with acetic acid giving the respective bromohydrins 8, 9, and 10 that were smoothly converted into the epoxides 11 [52,53,54], 12, and 13 (Scheme 1). Also, rac-2-(oxiranyl)pyridine (14) [55] was prepared analogously from 2-vinylpyridine.…”

Section: Resultsmentioning

confidence: 99%

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

Wosińska-Hrydczuk

Skarżewski

2019

Heteroatom Chemistry

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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.

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Section: Selective Epoxide Ring Opening: Pyridine Derivativesmentioning

confidence: 70%