Artículos de revistas
A Versatile Approach To Noncoded Beta-hydroxy-alpha-amino Esters And Alpha-amino Acids/esters From Morita-baylis-hillman Adducts
Registro en:
A Versatile Approach To Noncoded Beta-hydroxy-alpha-amino Esters And Alpha-amino Acids/esters From Morita-baylis-hillman Adducts. Georg Thieme Verlag Kg, v. 47, p. 113-123 JAN-2015.
0039-7881
WOS:000347380200014
10.1055/s-0034-1379168
Autor
Ullah
Hamid; Ferreira
Andre V.; Bendassolli
Jose A.; Rodrigues
Manoel T.
Jr.; Formiga
Andre Luiz B.; Coelho
Fernando
Institución
Resumen
Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) A simple and straightforward approach to the diastereoselective synthesis of noncoded beta-hydroxy-alpha-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 center dot nH(2)O/NaBH3CN led to the corresponding anti-beta-hydroxy-alpha-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 alpha-amino esters/acids and DOPA. 47 1
113 123 Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)