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Synthesis and Reactivity of β‐Bromo‐β‐Substituted Dehydroalanines
Author(s) -
Ferreira Paula M. T.,
Monteiro Luís S.
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600094
Subject(s) - dehydroalanine , chemistry , nucleophile , dichloromethane , reactivity (psychology) , derivative (finance) , medicinal chemistry , stereochemistry , catalysis , organic chemistry , peptide , medicine , biochemistry , alternative medicine , pathology , solvent , financial economics , economics
The methyl ester of N ‐ tert ‐butoxycarbonyl‐( Z )‐β‐bromo‐β‐(1,2,4‐triazol‐1‐yl)dehydroalanine was prepared by treatment of the methyl ester of N ‐ tert ‐butoxycarbonyl‐( E )‐β‐(1,2,4‐triazol‐1‐yl)dehydroalanine with N ‐bromosuccinimide (NBS), followed by Et 3 N. The reactivities of this compound and of our previously synthesized methyl ester of N ‐ tert ‐butoxycarbonyl‐β,β‐dibromodehydroalanine towards several nucleophiles were studied, and it was found that these compounds react with oxygen nucleophiles to give the corresponding α‐alkoxy‐β,β‐disubstituted alanines. Addition to the α‐carbon atom also occurred when the β,β‐dibromodehydroalanine derivative was treated with primary amines, giving α‐amino‐β,β‐dibromoalanines. Treatment of the β‐bromo‐β‐(1,2,4‐triazol‐1‐yl)dehydroalanine derivative with amines gave α‐(alkylamino)‐β‐(alkylimino)alanines in high yields. These iminoalanines afforded α‐aminoglycines when treated with silica in dichloromethane. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)