Literature DB >> 18370392

New chemistry with old functional groups: on the reaction of isonitriles with carboxylic acids--a route to various amide types.

Xuechen Li1, Samuel J Danishefsky.   

Abstract

Thermolysis of isonitriles with carboxylic acids provides, in one step, N-formyl imides (see, for example, 8 + 19 --> 21). The resultant N-formyl group can be converted to N-H, NCH2OH, or NCH3. This chemistry allows for a new route for synthesizing beta-N (asparagine)-linked glycosyl amino acids.

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Year:  2008        PMID： 18370392      PMCID： PMC2580817          DOI： 10.1021/ja800612r

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  21 in total

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10.  Selective reduction of anomeric azides to amines with tetrathiomolybdate: synthesis of beta-D-glycosylamines.

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  33 in total

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3.  Reaction of isonitriles with carboxylic acids in a cavitand: observation of elusive isoimide intermediates.

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Review 4.  A fascinating journey into history: exploration of the world of isonitriles en route to complex amides.

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6.  Umpolung reactivity in amide and peptide synthesis.

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7.  Addressing mechanistic issues in the coupling of isonitriles and carboxylic acids: potential routes to peptidic constructs.

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8.  On the two-component microwave-mediated reaction of isonitriles with carboxylic acids: regarding alleged formimidate carboxylate mixed anhydrides.

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Journal:  J Am Chem Soc       Date:  2008-09-11       Impact factor: 15.419

9.  Reaction of thioacids with isocyanates and isothiocyanates: a convenient amide ligation process.

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10.  Thio FCMA intermediates as strong acyl donors: a general solution to the formation of complex amide bonds.

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