Highly enantioselective synthesis of α-azido-β-hydroxy methyl ketones catalyzed by a cooperative proline-guanidinium salt system

Highly enantioselective synthesis of α-azido-β-hydroxy methyl ketones catalyzed by a cooperative proline-guanidinium salt system

The combined activity of (S)-proline and an achiral tetraphenylborate TBD-derived guanidinium salt permits the aldol reaction between azidoacetone and aromatic, or heteroaromatic aldehydes. The α-azido-β-hydroxy methyl ketones obtained as products can be isolated in good yield, with high diastereo-...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2014-03, Vol.50 (20), p.2598-2600
Hauptverfasser: Martínez-Castañeda, Ángel, Kędziora, Kinga, Lavandera, Iván, Rodríguez-Solla, Humberto, Concellón, Carmen, del Amo, Vicente
Format: Artikel
Sprache:eng
Schlagworte:
Aldehydes
Azides - chemical synthesis
Azides - chemistry
Catalysis
Guanidine - chemistry
Ketones
Ketones - chemical synthesis
Ketones - chemistry
Methylation
Molecular Structure
Proline - chemistry
Stereoisomerism
Synthesis (chemistry)
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Beschreibung
Zusammenfassung:The combined activity of (S)-proline and an achiral tetraphenylborate TBD-derived guanidinium salt permits the aldol reaction between azidoacetone and aromatic, or heteroaromatic aldehydes. The α-azido-β-hydroxy methyl ketones obtained as products can be isolated in good yield, with high diastereo- and enantioselectivity.
ISSN:1359-7345
1364-548X
DOI:10.1039/c3cc49371g