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Stereoselective synthesis of functional dehydrophenylalanine derivatives from novel β-chloroamino esters

✍ Scribed by Brahim Ould Elemine; Mohamed Rached Ennigrou; Rafâa Besbes

Publisher
John Wiley and Sons
Year
2011
Tongue
English
Weight
233 KB
Volume
23
Category
Article
ISSN
1042-7163

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✦ Synopsis

Abstract

New functional dehydrophenylalanines 3 were prepared from β‐amino alcohols 1 in a two‐step reaction sequence. The synthesis involved chlorination of the starting amino alcohols 1 to afford the intermediate erythro β‐chloroamines 2. Treatment of the latter with an appropriate base led to a highly stereoselective elimination reaction, giving the corresponding (E)‐dehydrophenylalanine derivatives 3 in high yields. © 2011 Wiley Periodicals, Inc. Heteroatom Chem 23:91–98, 2012; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.20756

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