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- and enantioselectivity.
Departamento de Química Orgánica e Inorgánica, Universidad de Oviedo, C/Julián Clavería 8, 33006, Oviedo, Spain. ccf@uniovi.es vdelamo@uniovi.es.
Ángel
Á
Martínez-Castañeda
Kinga
K
Kędziora
Iván
I
Lavandera
Humberto
H
Rodríguez-Solla
Carmen
C
Concellón
Vicente
V
del Amo
D001386:Azides / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D019791:Guanidine / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry*; D008745:Methylation; D015394:Molecular Structure; D011392:Proline / Q000737:chemistry*; D013237:Stereoisomerism
D001386:Azides; D007659:Ketones; D011392:Proline; D019791:Guanidine