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alpha-Amidoalkylating agents from N-acyl-alpha-amino acids: 1-(N-acylamino)alkyltriphenylphosphonium salts.
MedLine Citation:
PMID:  22250978     Owner:  NLM     Status:  Publisher    
N-Acyl-alpha-amino acids were efficiently transformed in a two-step procedure into 1-N-(acylamino)alkyltriphenylphosphonium salts - new powerful alpha-amidoalkylating agents. The effect of the alpha-amino acid structure, the base used [MeONa, or a silica gel-supported piperidine (SiO2-Pip)], and the main electrolysis parameters (current density, charge consumption) on the yield and selectivity of the electrochemical decarboxylative alpha-methoxylation of N acyl-alpha-amino acids (Hofer-Moest reaction) was investigated. For most proteinogenic and all studied unproteinogenic alpha-amino acids, very good results were obtained using a substoichiometric amount of SiO2-Pip as the base. Only in the case of N acylated cysteine, methionine and tryptophan attempts to carry out the Hofer-Moest reaction in the applied conditions failed, probably because of the susceptibility of these alpha-amino acids to an electrochemical oxidation. The methoxy group of N (1 methoxyalkyl)amides was effectively displaced with the triphenylphosphonium group by dissolving an equimolar amount of N (1-methoxyalkyl)amide and triphenylphosphonium tetrafluoroborate in CH2Cl2 at room temperature for 30 minutes, followed by the precipitation of 1-N-(acylamino)alkyltriphenylphosphonium salt with Et2O.
Roman Mazurkiewicz; Jakub Adamek; Agnieszka Październiok-Holewa; Katarzyna Zielińska; Wojciech Simka; Anna Gajos; Karol Szymura
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2012-1-16
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  -     ISSN:  1520-6904     ISO Abbreviation:  -     Publication Date:  2012 Jan 
Date Detail:
Created Date:  2012-1-18     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
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