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A convenient samarium-promoted synthesis of aliphatic (E)-nitroalkenes under mild conditions
José M Concellón1, Pablo L Bernad, Humberto Rodríguez-Solla
1Departamento Química Orgánica e Inorgánica, Universidad de Oviedo, JuliAn Clavería 8, 33071 Oviedo, Spain. jmcg@uniovi.es
Abstract:
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.
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