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Carboxyl-modified amino acids and peptides: I) An efficient method for the synthesis of monofunctionalized enamines and monofunctionalized methyl ketone derivatives from thioamides via episulfides and thioiminium salts

✍ Scribed by Gilles Sauvé; Tarek S. Mansour; Paule Lachance; Bernard Belleau

Publisher: Elsevier Science
Year: 1988
Tongue: French
Weight: 253 KB
Volume: 29
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)86041-4

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✦ Synopsis

Thioamides 4 were transformed by two convenient routes to various functionalized enamines 7 containing different electron-withdrawing groups E which on subsequent hydrolysis gave the corresponding methyl ketone derivatives 8.

Application of this methodology to obtain modified dipeptides at the carboxyl end, the determination of stereochemistry and the degree of racemization are discussed.

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Carboxyl-modified amino acids and peptides: II) A convenient route for the synthesis of difunctionalized enamines from thioamides via thioiminium salts

✍ Gilles Sauvé; Nicolas Le Berre; Boulos Zacharie 📂 Article 📅 1988 🏛 Elsevier Science 🌐 French ⚖ 218 KB

From thioamides 4. via thioiminium salts 5, various difunctionalized enamines 6 with different electron-withdrawing groups E, E' (E: CN, CO,Me, COR, SO,R, etc; El: CN, CO,Me) are prepared. Application of the methodology, the determination of stereochemistry and the degree of racemization of some ami