Literature DB >> 18698780

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

Per Restorp1, Julius Rebek.   

Abstract

A deep cavitand with an inwardly directed carboxylic acid function reacts with small aliphatic isonitriles to form N-acyl formamides inside the cavity. The unique isolation and stabilization of covalently bound guests within the structured environment of the cavitand allows for observation of the labile O-acyl isoimide intermediate using conventional spectroscopic methods.

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Year:  2008        PMID： 18698780      PMCID： PMC2642476          DOI： 10.1021/ja803854r

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


  28 in total

1.  Selectivity in an encapsulated cycloaddition reaction.

Authors:  Jian Chen; Julius Rebek
Journal:  Org Lett       Date:  2002-02-07       Impact factor: 6.005

2.  A functionalized, deep cavitand catalyzes the aminolysis of a choline derivative.

Authors:  Arnaud Gissot; Julius Rebek
Journal:  J Am Chem Soc       Date:  2004-06-23       Impact factor: 15.419

3.  Fluorous nanodroplets structurally confined in an organopalladium sphere.

Authors:  Sota Sato; Junya Iida; Kosuke Suzuki; Masaki Kawano; Tomoji Ozeki; Makoto Fujita
Journal:  Science       Date:  2006-09-01       Impact factor: 47.728

Review 4.  Functional cavitands: chemical reactivity in structured environments.

Authors:  Byron W Purse; Julius Rebek
Journal:  Proc Natl Acad Sci U S A       Date:  2005-07-25       Impact factor: 11.205

5.  A deep cavitand catalyzes the Diels-Alder reaction of bound maleimides.

Authors:  Richard J Hooley; Julius Rebek
Journal:  Org Biomol Chem       Date:  2007-10-04       Impact factor: 3.876

6.  A cavitand stabilizes the Meisenheimer complex of SNAr reactions.

Authors:  Sara M Butterfield; Julius Rebek
Journal:  Chem Commun (Camb)       Date:  2007-03-19       Impact factor: 6.222

7.  Cavitands: organic hosts with enforced cavities.

Authors:  D J Cram
Journal:  Science       Date:  1983-03-11       Impact factor: 47.728

8.  Detection of reactive tetrahedral intermediates in a deep cavitand with an introverted functionality.

Authors:  Richard J Hooley; Tetsuo Iwasawa; Julius Rebek
Journal:  J Am Chem Soc       Date:  2007-11-16       Impact factor: 15.419

9.  Self-fulfilling cavitands: packing alkyl chains into small spaces.

Authors:  Byron W Purse; Julius Rebek
Journal:  Proc Natl Acad Sci U S A       Date:  2006-02-13       Impact factor: 11.205

10.  Reactivity and molecular recognition: amine methylation by an introverted ester.

Authors:  Byron W Purse; Pablo Ballester; Julius Rebek
Journal:  J Am Chem Soc       Date:  2003-12-03       Impact factor: 15.419
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  12 in total

Review 1.  A fascinating journey into history: exploration of the world of isonitriles en route to complex amides.

Authors:  Rebecca M Wilson; Jennifer L Stockdill; Xiangyang Wu; Xuechen Li; Paul A Vadola; Peter K Park; Ping Wang; Samuel J Danishefsky
Journal:  Angew Chem Int Ed Engl       Date:  2012-02-24       Impact factor: 15.336

2.  Preparative scale and convenient synthesis of a water-soluble, deep cavitand.

Authors:  Simone Mosca; Yang Yu; Julius Rebek
Journal:  Nat Protoc       Date:  2016-07-07       Impact factor: 13.491

3.  Solid-phase peptide synthesis and solid-phase fragment coupling mediated by isonitriles.

Authors:  Ting Wang; Samuel J Danishefsky
Journal:  Proc Natl Acad Sci U S A       Date:  2013-07-02       Impact factor: 11.205

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

Authors:  Xuechen Li; Yu Yuan; Cindy Kan; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2008-09-11       Impact factor: 15.419

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

Authors:  Xuechen Li; Yu Yuan; William F Berkowitz; Louis J Todaro; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2008-09-11       Impact factor: 15.419

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

Authors:  David Crich; Kaname Sasaki
Journal:  Org Lett       Date:  2009-08-06       Impact factor: 6.005

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

Authors:  Yu Rao; Xuechen Li; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2009-09-16       Impact factor: 15.419

8.  Cavitands with mobile walls.

Authors:  Shengxiong Xiao; Dariush Ajami; Julius Rebek
Journal:  Org Lett       Date:  2009-08-06       Impact factor: 6.005

9.  Revisiting oxytocin through the medium of isonitriles.

Authors:  Ting Wang; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2012-08-02       Impact factor: 15.419

Review 10.  Chemistry and catalysis in functional cavitands.

Authors:  Richard J Hooley; Julius Rebek
Journal:  Chem Biol       Date:  2009-03-27
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