Literature DB >> 11878965

Asymmetric azidation-cycloaddition with open-chain peptide-based catalysts. A sequential enantioselective route to triazoles.

David J Guerin1, Scott J Miller.   

Abstract

A family of beta-substituted histidine-containing peptides has been synthesized to probe the effect of noncovalent conformational rigidification on catalyst enantioselectivity. Unambiguous enhancement of enantioselectivity in the conjugate addition of azide to alpha,beta-unsaturated carboxylate derivatives has been achieved, enabling application to a sequential asymmetric azidation/cycloaddition for the synthesis of optically enriched triazoles and triazolines.

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Year:  2002        PMID： 11878965     DOI： 10.1021/ja0177814

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


  10 in total

1.  Asymmetric aza-Michael reactions of alpha,beta-unsaturated ketones with bifunctional organic catalysts.

Authors:  Xiaojie Lu; Li Deng
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

2.  Practical and highly enantioselective synthesis of beta-alkynyl-beta-amino esters through Ag-catalyzed asymmetric mannich reactions of silylketene acetals and alkynyl imines.

Authors:  Nathan S Josephsohn; Emma L Carswell; Marc L Snapper; Amir H Hoveyda
Journal:  Org Lett       Date:  2005-06-23       Impact factor: 6.005

3.  Enantioselective, Stereodivergent Hydroazidation and Hydroamination of Allenes Catalyzed by Acyclic Diaminocarbene (ADC) Gold(I) Complexes.

Authors:  Dimitri A Khrakovsky; Chuanzhou Tao; Miles W Johnson; Richard T Thornbury; Sophia L Shevick; F Dean Toste
Journal:  Angew Chem Int Ed Engl       Date:  2016-04-20       Impact factor: 15.336

4.  Allylic C-H amination for the preparation of syn-1,3-amino alcohol motifs.

Authors:  Grant T Rice; M Christina White
Journal:  J Am Chem Soc       Date:  2009-08-26       Impact factor: 15.419

5.  Proline editing: a general and practical approach to the synthesis of functionally and structurally diverse peptides. Analysis of steric versus stereoelectronic effects of 4-substituted prolines on conformation within peptides.

Authors:  Anil K Pandey; Devan Naduthambi; Krista M Thomas; Neal J Zondlo
Journal:  J Am Chem Soc       Date:  2013-03-11       Impact factor: 15.419

6.  A Selenourea-Thiourea Brønsted Acid Catalyst Facilitates Asymmetric Conjugate Additions of Amines to α,β-Unsaturated Esters.

Authors:  Yingfu Lin; William J Hirschi; Anuj Kunadia; Anirudra Paul; Ion Ghiviriga; Khalil A Abboud; Rachael W Karugu; Mathew J Vetticatt; Jennifer S Hirschi; Daniel Seidel
Journal:  J Am Chem Soc       Date:  2020-03-11       Impact factor: 15.419

7.  Theoretical study of the catalysis of cyanohydrin formation by the cyclic dipeptide catalyst cyclo[(S)-His-(S)-Phe].

Authors:  Franziska Schoenebeck; K N Houk
Journal:  J Org Chem       Date:  2009-02-20       Impact factor: 4.354

8.  Calcium(ii)-catalyzed enantioselective conjugate additions of amines.

Authors:  Brice E Uno; Rachel D Dicken; Louis R Redfern; Charlotte M Stern; Greg G Krzywicki; Karl A Scheidt
Journal:  Chem Sci       Date:  2018-01-10       Impact factor: 9.825

9.  Divergent synthesis of chiral cyclic azides via asymmetric cycloaddition reactions of vinyl azides.

Authors:  Nuligonda Thirupathi; Fang Wei; Chen-Ho Tung; Zhenghu Xu
Journal:  Nat Commun       Date:  2019-07-18       Impact factor: 14.919

10.  Asymmetric Azidation under Hydrogen Bonding Phase-Transfer Catalysis: A Combined Experimental and Computational Study.

Authors:  Jimmy Wang; Matthew A Horwitz; Alexander B Dürr; Francesco Ibba; Gabriele Pupo; Yuan Gao; Paolo Ricci; Kirsten E Christensen; Tejas P Pathak; Timothy D W Claridge; Guy C Lloyd-Jones; Robert S Paton; Véronique Gouverneur
Journal:  J Am Chem Soc       Date:  2022-03-01       Impact factor: 15.419
  10 in total

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