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The hetero-Diels–Alder addition of ethyl 2-nitrosoacrylate to electron-rich alkenes as a route to unnatural α-amino acids

✍ Scribed by John K Gallos; Vassiliki C Sarli; Anastassia C Varvogli; Constantina Z Papadoyanni; Sofia D Papaspyrou; Nicolaos G Argyropoulos

Book ID: 104253589
Publisher: Elsevier Science
Year: 2003
Tongue: French
Weight: 182 KB
Volume: 44
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(03)00836-0

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✦ Synopsis

A new method for the stereoselective synthesis of nonproteinogenic a-amino acids has been developed, which involves hetero-Diels-Alder addition of ethyl 2-nitrosoacrylate to electron-rich alkenes, such as enol ethers, enamines and allylsilanes, and a further two or three step manipulation of the resulting oxazines.

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