ChemInform Abstract: 1,2-Asymmetric Induction in Radical Reactions of β-Amino Acid Derivatives.

ChemInform ◽  
2010 ◽  
Vol 26 (45) ◽  
pp. no-no
Author(s):  
E. P. KUENDIG ◽  
L.-H. XU ◽  
P. ROMANENS
Keyword(s):  
Amino Acid ◽  
Asymmetric Induction ◽  
Radical Reactions ◽  
Amino Acid Derivatives

1,2-Asymmetric induction in radical reactions of β-amino acid derivatives

1995 ◽  
Vol 36 (23) ◽  
pp. 4047-4050 ◽  
Author(s):  
E. Peter Kündig ◽  
Long-He Xu ◽  
Patrick Romanens
Keyword(s):  
Amino Acid ◽  
Asymmetric Induction ◽  
Radical Reactions ◽  
Amino Acid Derivatives

Reactions of α-Substituted Glycine Derivatives With Stannanes in the Presence of Disulfides

1994 ◽  
Vol 47 (5) ◽  
pp. 859 ◽  
Author(s):  
CJ Easton ◽  
SC Peters
Keyword(s):  
Amino Acid ◽  
Disulfide Bonds ◽  
Radical Reactions ◽  
Amino Acid Derivatives ◽  
Benzyl Radical ◽  
Mixed Disulfide ◽  
Diphenyl Disulfide ◽  
Glycine Derivatives ◽  
Chemical Integrity ◽  
Homolytic Substitution

Reactions of α- bromo -, α- benzoyloxy - and α- methoxy -substituted glycine derivatives with stannanes afforded the corresponding α- centred glycinyl radical, which reacted with di -t-butyl disulfide and diphenyl disulfide by homolytic substitution to give the corresponding α-t- butylthio- and α-phenylthio -substituted glycine derivatives, respectively. The glycinyl radical reacted with dibenzyl disulfide by displacement of benzyl radical to give a mixed disulfide, which was subsequently reduced to the corresponding α- benzylthio-substituted glycine derivative. In related reactions of a cystine derivative the corresponding S-glycinylcysteine derivative was produced, indicating that, while the chemical integrity of disulfide bonds in cystine derivatives is likely to be affected in radical reactions of peptides, the reactions are suitable for exploitation in the synthesis of cross-linked amino acid derivatives.

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