Efficient addition reaction of bromonitromethane to aldehydes catalyzed by NaI: a new route to 1-bromo-1-nitroalkan-2-ols under very mild conditions.
[Structure: see text] A catalytic NaI-mediated novel synthesis of 1-bromo-1-nitroalkan-2-ols was carried out by reaction of bromonitromethane with a variety of aldehydes, under very mild conditions. When the reaction was performed with chiral N,N-dibenzyl alaninal, the corresponding enantiopure (1S,2S,3S)-3-dibenzylamino-1-bromo-1-nitrobutan-2-ol was obtained with good stereoselectivity. The structure of this enantiopure bromohydrin was established by X-ray analysis.
Concellón
José M
JM
Departamento de Química Orgánica e Inorgánica, Facultad de Química, Universidad de Oviedo, Spain. jmcg@fq.uniovi.es
Rodríguez-Solla
Humberto
H
Concellón
Carmen
C
García-Granda
Santiago
S
Díaz
M Rosario
MR