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

JM Concellón, H Rodríguez-Solla…

Index: Concellon, Jose M.; Rodriguez-Solla, Humberto; Concellon, Carmen Journal of Organic Chemistry, 2006 , vol. 71, # 20 p. 7919 - 7922

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Citation Number: 28

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.