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DOI: 10.1055/s-0034-1379168
A Versatile Approach to Noncoded β-Hydroxy-α-amino Esters and α-Amino Acids/Esters from Morita–Baylis–Hillman Adducts
Publikationsverlauf
Received: 09. Juli 2014
Accepted after revision: 26. August 2014
Publikationsdatum:
02. Oktober 2014 (online)


Abstract
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.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- Supporting Information