Journal of Organic Chemistry (2019)
Update date:2022-08-15
Topics:
Baro, Angelika
Dallavalle, Sabrina
Hasnik, Fabian
Laschat, Sabine
Sinast, Moritz
Sube, Tobias
Wischnat, Jonathan
Zuccolo, Marco
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.
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