A convenient samarium-promoted synthesis of aliphatic (E)-nitroalkenes under mild conditions.
A samarium-promoted synthesis of (E)-nitroalkenes from 1-bromo-1-nitroalkan-2-ols in high yields and with total selectivity is reported. This reaction together with the easy and efficient preparation of the 1-bromo-1-nitroalkan-2-ols constitutes a simple and advantageous alternative toward nitroalkenes with total E-stereoselectivity. A mechanism is proposed to explain the E-stereoselectivity of the beta-elimination reaction.
Concellón
José M
JM
Departamento Química Orgánica e Inorgánica, Universidad de Oviedo, JuliAn Clavería 8, 33071 Oviedo, Spain. jmcg@uniovi.es
Bernad
Pablo L
PL
Rodríguez-Solla
Humberto
H
Concellón
Carmen
C