1038432-24-4Relevant articles and documents
A versatile approach to noncoded β-hydroxy-α-amino esters and α-amino acids/esters from morita-baylis-hillman adducts
Ullah, Hamid,Ferreira, Andr V.,Bendassolli, Jos A.,Rodrigues, Manoel T.,Formiga, Andr Luiz B.,Coelho, Fernando
, p. 113 - 123 (2015/02/02)
A simple and straightforward approach to the diastereoselective synthesis of noncoded β-hydroxy-α-amino esters from Morita-Baylis-Hillman (MBH) adducts is described. The strategy is based on a one-pot sequence involving an oxidative cleavage of the double bond of silylated Morita-Baylis-Hillman adducts, followed by the reaction with hydroxylamine hydrochloride/pyridine to form oximes. The stereoselective reduction of the oximes with the mixture MoCl5·nH2O/NaBH3CN led to the corresponding anti-β-hydroxy-α-amino esters in four steps in good overall yield and with diastereoselectivity higher than 95%. A slight modification of the synthetic approach has allowed for the racemic synthesis of a set of noncoded α-amino esters/acids and DOPA
Diastereoselective approach to substituted oxazolidinones from Morita-Baylis-Hillman adducts
Rezende, Patricia,Paioti, Paulo H. S.,Coelho, Fernando
experimental part, p. 227 - 242 (2011/03/19)
We disclose herein a new strategy for the diastereoselective preparation of 4- and 4,5-substituted oxazolidinones from Morita-Baylis-Hillman adducts. The strategy is based on an intramolecular cyclization involving a nucleophilic attack of an alkoxide ion
Acyloins from Morita-Baylis-Hillman adducts: an alternative approach to the racemic total synthesis of bupropion
Amarante, Giovanni W.,Rezende, Patrícia,Cavallaro, Mayra,Coelho, Fernando
, p. 3744 - 3748 (2008/09/21)
In this Letter, we describe an easy and straightforward strategy for the preparation of acyloins (α-hydroxyketones) from Morita-Baylis-Hillman adducts, based on a Curtius rearrangement. Different acyloins were obtained with good overall yield (>40% for three steps). To exemplify the synthetic usefulness of this strategy, total synthesis of (±)-bupropion, a dopamine, and nor-epinefrine reuptake inhibitor has been accomplished in eight steps with an overall yield of 25%.