NDLI: Efficient Amide Bond Formation through a Rapid and Strong Activation of Carboxylic Acids in a Microflow Reactor**

Content Provider	PubMed Central
Author	Fuse, Shinichiro Mifune, Yuto Takahashi, Takashi
Copyright Year	2014
Abstract	The development of highly efficient amide bond forming methods which are devoid of side reactions, including epimerization, is important, and such a method is described herein and is based on the concept of rapid and strong activation of carboxylic acids. Various carboxylic acids are rapidly (0.5 s) converted into highly active species, derived from the inexpensive and less-toxic solid triphosgene, and then rapidly (4.3 s) reacted with various amines to afford the desired peptides in high yields (74 %–quant.) without significant epimerization (≤3 %). Our process can be carried out at ambient temperature, and only CO2 and HCl salts of diisopropylethyl amine are generated. In the long history of peptide synthesis, a significant number of active coupling reagents have been abandoned because the highly active electrophilic species generated are usually susceptible to side reactions such as epimerization. The concept presented herein should renew interest in the use of these reagents.
Related Links	http://dx.doi.org/10.1002/anie.201307987
Ending Page	855
Page Count	5
Starting Page	851
File Format	PDF
ISSN	14337851
e-ISSN	15213773
Journal	Angewandte Chemie (International Ed. in English)
Issue Number	3
Volume Number	53
Language	English
Publisher	WILEY-VCH Verlag
Publisher Date	2014-01-13
Access Restriction	Open
Rights Holder	WILEY-VCH Verlag
Subject Keyword	Chemistry(all) Catalysis Research in Higher Education
Content Type	Text
Resource Type	Article
Subject	Chemistry Catalysis

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