Efficient Nitro-Aldol Reaction Using SmI₂: A New Route to Nitro Alcohols under Very Mild Conditions

José M. Concellón,* Humberto Rodríguez-Solla, and Carmen Concellón

*Departamento de Química Orgnica e Inorgnica, Facultad de Química, Universidad de Oviedo, Julin Clavería 8, 33071 Oviedo, Spain, Email: jmcguniovi.es

J. M. Concellón, H. Rodríguez-Solla, C. Concellón, J. Org. Chem., 2006, 71, 7919-7922.

DOI: 10.1021/jo061465w

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Abstract

Racemic 1-nitroalkan-2-ols are obtained by reaction of bromonitromethane with a variety of aldehydes promoted by SmI₂. Chiral N,N-dibenzyl amino aldehydes afford the corresponding enantiopure 3-amino-1-nitroalkan-2-ols with good diastereoselectivity.

see article for more examples

proposed mechanism

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Efficient Nitro-Aldol Reaction Using SmI₂: A New Route to Nitro Alcohols under Very Mild Conditions

J. M. Concellón, C. Concellón, J. Org. Chem., 2006, 71, 4428-4432.

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Key Words

Nitro compounds, Samarium Diiodide

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ID: J42-Y2006-3110