Efficient nitro-aldol reaction using SmI2: a new route to nitro alcohols under very mild conditions.

J Org Chem

Departamento de Química Organica e Inorganica, Facultad de Química, Universidad de Oviedo, Julian Clavería 8, 33071 Oviedo, Spain.

Published: September 2006

AI Article Synopsis

  • A new approach is introduced for creating racemic 1-nitroalkan-2-ols by reacting bromonitromethane with different aldehydes using SmI2 as a catalyst.
  • This method also allows for the synthesis of chiral compounds using chiral N,N-dibenzyl amino aldehydes.
  • The process yields enantiopure 3-amino-1-nitroalkan-2-ols with high selectivity for their stereochemistry.

Article 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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http://dx.doi.org/10.1021/jo061465wDOI Listing

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Efficient nitro-aldol reaction using SmI2: a new route to nitro alcohols under very mild conditions.

J Org Chem

September 2006

Departamento de Química Organica e Inorganica, Facultad de Química, Universidad de Oviedo, Julian Clavería 8, 33071 Oviedo, Spain.

Article Synopsis
  • A new approach is introduced for creating racemic 1-nitroalkan-2-ols by reacting bromonitromethane with different aldehydes using SmI2 as a catalyst.
  • This method also allows for the synthesis of chiral compounds using chiral N,N-dibenzyl amino aldehydes.
  • The process yields enantiopure 3-amino-1-nitroalkan-2-ols with high selectivity for their stereochemistry.
View Article and Find Full Text PDF

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