Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 132, Issue 14, Pages 5002-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja101292a
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Funding
- Abbott Young Investigator Award
- Arun Guthikonda Memorial Graduate Fellowship
- Novartis Summer Undergraduate Research Fellowship
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The first example of aromatic cation-activated nucleophilic acyl substitution has been achieved. The conversion of carboxylic acids to their corresponding acid chlorides occurs rapidly in the presence of 3,3-dichlorocyclopropenes via the intermediacy of cyclopropenium carboxylate complexes. The effect of cyclopropene substituents on the rate of conversion is examined. The addition of tertiary amine base is found to dramatically accelerate reaction, and conditions were developed for the preparation of acid sensitive acid chlorides. Preparative scale peptide couplings of two N-Boc amino acids were achieved with this method.
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