Samarium Iodide-Promoted Asymmetric Reformatsky Reaction of 3-(2-Haloacyl)-2-oxazolidinones with Enals

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...

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Vydané v:Journal of organic chemistry Ročník 84; číslo 16; s. 10050 - 10064
Hlavní autori: Sinast, Moritz, Zuccolo, Marco, Wischnat, Jonathan, Sube, Tobias, Hasnik, Fabian, Baro, Angelika, Dallavalle, Sabrina, Laschat, Sabine
Médium: Journal Article
Jazyk:English
Vydavateľské údaje: WASHINGTON Amer Chemical Soc 16.08.2019
Predmet:
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
DIIODIDE
OXIDATION
ORGANIC-SYNTHESIS
REAGENTS
CHIRAL ALPHA-BROMOACETYL-2-OXAZOLIDINONES
COUPLING REACTIONS
AMINO-ACIDS
ANTI-ALDOL REACTIONS
ALDEHYDES
DERIVATIVES
ISSN:0022-3263, 1520-6904, 1520-6904
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Popis
Shrnutí: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.
Bibliografia:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.9b01219