A new strategy for the stereoselective synthesis of unnatural α-amino acids
…, CZ Papadoyanni, SD Papaspyrou, NG Argyropoulos
Index: Gallos, John K.; Sarli, Vassiliki C.; Massen, Zoe S.; Varvogli, Anastassia C.; Papadoyanni, Constantina Z.; Papaspyrou, Sofia D.; Argyropoulos, Nicolaos G. Tetrahedron, 2005 , vol. 61, # 3 p. 565 - 574
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Citation Number: 44
Abstract
A new method for the synthesis of racemic non-proteinogenic α-amino acids has been developed, which involves (i) hetero-Diels–Alder addition of ethyl 2-nitrosoacrylate to electron rich alkenes such as enol ethers, enamines and allylsilanes,(ii) NaCNBH3 reduction of the CN bond in the oxazines thus generated, the stereochemistry of the products being controlled by epimerisation of the thermodynamically less stable isomer to ...