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

Supporting Info

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

Departamento de Qumica Orgnica e Inorgnica, Facultad de Qumica, Universidad de Oviedo, Julin Clavera 8, 33071 Oviedo, Spain jmcg@fq.uniovi.es

J. Org. Chem., 2006, 71 (20), pp 7919–7922

DOI: 10.1021/jo061465w

Publication Date (Web): August 31, 2006

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

A novel method to obtain racemic 1-nitroalkan-2-ols by reaction of bromonitromethane with a variety of aldehydes and promoted by SmI₂ is reported. On the basis of these results, the chiral version has also been performed with chiral N,N-dibenzyl amino aldehydes, affording the corresponding enantiopure 3-amino-1-nitroalkan-2-ols with good stereoselectivity.

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