A Versatile Approach to Noncoded beta-Hydroxy-alpha-amino Esters and alpha-Amino Acids/Esters from Morita-Baylis-Hillman Adducts

作者：Ullah Hamid; Ferreira Andre V; Bendassolli Jose A; Rodrigues Manoel T Jr; Formiga Andre Luiz B; Coelho Fernando^*

来源：Synthesis (Germany), 2015, 47(1): 113-123.

DOI：10.1055/s-0034-1379168

• Morita-Baylis-Hillman adducts
• amino acids
• reduction
• diastereoselectivity
• DOPA

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.

• 出版日期2015-1