281195-11-7Relevant academic research and scientific papers
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
Heterocycles from Morita-Baylis-Hillman adducts: Synthesis of 5-oxopyrazolidines, arylidene-5-oxopyrazolidines, and oxo-2,5-dihydro-pyrazols
Correia, José Tiago M.,Rodrigues Jr., Manoel T.,Santos, Hugo,Tormena, Cláudio F.,Coelho, Fernando
, p. 826 - 832 (2013/07/25)
Starting from Morita-Baylis-Hillman (MBH) adducts, an approach for the synthesis of oxopyrazolidines, arylidene-oxopyrazolidines, and oxo-2,5-dihydropyrazoles is described. The method is based on a tandem process involving a Michael addition of amino-guan
Ozonolysis of Morita-Baylis-Hillman adducts originated from aromatic aldehydes: an expeditious diastereoselective approach for the preparation of α,β-dihydroxy-esters
Abella, Carlos A.M.,Rezende, Patrícia,Lino de Souza, Michele F.,Coelho, Fernando
, p. 145 - 148 (2008/04/13)
We disclose herein ozonolysis of Morita-Baylis-Hillman adducts originated from aromatic aldehydes. This efficient reaction provides α-ketoesters with different substitution patterns on the aromatic ring. Diastereoselective reduction of the corresponding α-ketoester obtained in the oxidative cleavage step provides α,β-dihydroxy-esters with excellent degree of anti diastereoselection. The method is simple and easy to execute and is therefore a valuable alternative to prepare either α-ketoesters or α,β-dihydroxy-esters.
Antiproliferative effect of?Baylis-Hillman adducts and?a?new phthalide derivative on?human tumor cell lines
Kohn, Luciana K.,Pavam,Veronese,Coelho,De Carvalho,Almeida, Wanda P.
, p. 738 - 744 (2007/10/03)
In this work we report our results concerning the study on the in vitro antiproliferative activity of 18 Baylis-Hillman adducts and some derivatives against a panel of humor tumor cell lines. A brief qualitative structure-activity relationship study indicated that carbon-carbon double bond and the presence of an electron-withdrawing substituent at the aromatic ring are essential for the activity. A quinoline-phthalide derivative has exhibited a potent effect on the proliferation of all cell lines. It is interesting to note their special cytotoxic activity against NCIADR cell line.
Diastereoselective heterogeneous catalytic hydrogenation of Baylis- Hillman adducts
Mateus, Cristiano R.,Almeida, Wanda P.,Coelho, Fernando
, p. 2533 - 2536 (2007/10/03)
We describe herein our results concerning a highly diastereoselective heterogeneous hydrogenation of Baylis-Hillman adducts obtained from aromatic aldehydes. The results obtained are complementary to those already described for homogeneous catalytic hydro
