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- W2953129898 abstract "A stereoselective approach to the preparation of 7,5-fused bicyclic lactams based on Meyers’ lactamization is presented. The lactamization step is conducted at 0 °C with 6-oxohexanoic acid 1 and with various chiral aminoalcohols in the presence of 2-fluoro-1-ethylpyridinium tetrafluoroborate (FEP) as an activating agent. Under these mild conditions, bicyclic lactams 2–4 were obtained in satisfactory yields and diastereoselectivities up to 95%. To account for the high level of diastereoselection, the mechanistic aspects of Meyers’ lactamization were investigated by means of in situ infrared spectroscopy. Finally, the lactam enolate derived from 2 was subjected to reaction with various electrophiles, furnishing the corresponding β-substituted oxazoloazepinones 5–9 in good yields (up to 86%) and in moderate to excellent diastereoselectivities ranging from 27% to 95% de." @default.
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- W2953129898 date "2009-05-05" @default.
- W2953129898 modified "2023-09-24" @default.
- W2953129898 title "ChemInform Abstract: New Advances in Stereoselective Meyers′ Lactamization. Application to the Diastereoselective Synthesis of β-Substituted Oxazoloazepinones." @default.
- W2953129898 cites W2116841480 @default.
- W2953129898 doi "https://doi.org/10.1002/chin.200918164" @default.
- W2953129898 hasPublicationYear "2009" @default.
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