Literature DB >> 20160954

Coupling reactions of hindered isonitriles and hindered alkyl thioacids: Mechanistic studies.

Jennifer L Stockdill1, Xiangyang Wu, Samuel J Danishefsky.   

Abstract

The coupling reaction between hindered thioacids and isonitriles is developed and described. The mechanism for the formation of the thiopyruvamide products is explored, and the method is applied to a selection of substrates.

Entities:  

Year:  2009        PMID： 20160954      PMCID： PMC2758784          DOI： 10.1016/j.tetlet.2009.06.129

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  9 in total

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

Authors:  Per Restorp; Julius Rebek
Journal:  J Am Chem Soc       Date:  2008-08-13       Impact factor: 15.419

2.  Preparation and reactions of N-thioformyl peptides from amino thioacids and isonitriles.

Authors:  Yu Yuan; Jianglong Zhu; Xuechen Li; Xiangyang Wu; Samuel J Danishefsky
Journal:  Tetrahedron Lett       Date:  2009-05-20       Impact factor: 2.415

3.  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

4.  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

5.  The coupling of isonitriles and carboxylic acids occurring by sequential concerted rearrangement mechanisms.

Authors:  Gavin O Jones; Xuechen Li; Amy E Hayden; K N Houk; Samuel J Danishefsky
Journal:  Org Lett       Date:  2008-08-16       Impact factor: 6.005

6.  Reaction of carboxylic acids and isonitriles in small spaces.

Authors:  Jun-Li Hou; Dariush Ajami; Julius Rebek
Journal:  J Am Chem Soc       Date:  2008-05-29       Impact factor: 15.419

7.  Noncatalytic reaction of isonitriles and carboxylic acids en route to amide-type linkages.

Authors:  Xuechen Li; Samuel J Danishefsky
Journal:  Nat Protoc       Date:  2008       Impact factor: 13.491

8.  N-methylation of peptides: a new perspective in medicinal chemistry.

Authors:  Jayanta Chatterjee; Chaim Gilon; Amnon Hoffman; Horst Kessler
Journal:  Acc Chem Res       Date:  2008-07-18       Impact factor: 22.384

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

Authors:  Xuechen Li; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2008-03-28       Impact factor: 15.419
  9 in total
  7 in total

1.  Expanding the limits of isonitrile-mediated amidations: on the remarkable stereosubtleties of macrolactam formation from synthetic seco-cyclosporins.

Authors:  Xiangyang Wu; Jennifer L Stockdill; Peter K Park; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2012-01-17       Impact factor: 15.419

Review 2.  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

3.  Dihydro-3-(triphenylphosphoranylidene)-2,5-thiophendione: A Convenient Synthon for the Preparation of Substituted 1,4-Thiazepin-5-ones and Piperidinones via the Intermediacy of Thioacids.

Authors:  David Crich; Md Yeajur Rahaman
Journal:  Tetrahedron       Date:  2010-08-14       Impact factor: 2.457

4.  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

5.  On the synthesis of conformationally modified peptides through isonitrile chemistry: implications for dealing with polypeptide aggregation.

Authors:  Xiangyang Wu; Peter K Park; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2011-05-03       Impact factor: 15.419

6.  A Simple Method for the Conversion of Carboxylic Acids into Thioacids with Lawesson's Reagent.

Authors:  Yu Rao; Xuechen Li; Pavel Nagorny; Joji Hayashida; Samuel J Danishefsky
Journal:  Tetrahedron Lett       Date:  2009-12-02       Impact factor: 2.415

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
  7 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.