3-(2-Haloacyl)-2-oxazolidinones were shown to react with enals in an asymmetric SmI2-promoted Reformatsky reaction to give stereochemically well-defined 3-hydroxy-4-alkenyl- and 3-hydroxy-2-methyl-4-alkenyl imides. Chirality transfer of the Evans (S)-oxazolidinone unit via a Zimmerman-Traxler-like transition state resulted in Reformatsky products with a relative syn-configuration. The absolute configuration of compounds obtained is opposite to the corresponding products obtained via aldol addition of boron enolates to enals using the same Evans oxazolidinones.
Samarium iodide-promoted asymmetric Reformatsky reaction of 3-(2-Haloacyl)-2-oxazolidinones with enals / M. Sinast, M. Zuccolo, J. Wischnat, T. Sube, F. Hasnik, A. Baro, S. Dallavalle, S. Laschat. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 84:16(2019 Aug 16), pp. 10050-10064.
Samarium iodide-promoted asymmetric Reformatsky reaction of 3-(2-Haloacyl)-2-oxazolidinones with enals
M. Zuccolo;S. Dallavalle;
2019
Abstract
3-(2-Haloacyl)-2-oxazolidinones were shown to react with enals in an asymmetric SmI2-promoted Reformatsky reaction to give stereochemically well-defined 3-hydroxy-4-alkenyl- and 3-hydroxy-2-methyl-4-alkenyl imides. Chirality transfer of the Evans (S)-oxazolidinone unit via a Zimmerman-Traxler-like transition state resulted in Reformatsky products with a relative syn-configuration. The absolute configuration of compounds obtained is opposite to the corresponding products obtained via aldol addition of boron enolates to enals using the same Evans oxazolidinones.File | Dimensione | Formato | |
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