Literature DB >> 19655047

Stereoselective Synthesis of Quaternary Proline Analogues.

M Isabel Calaza1, Carlos Cativiela.   

Abstract

This review describes available methods for the diastereoselective and asymmetric synthesis of quaternary prolines. The focus is on the preparation of alpha-functionalized prolines with the pyrrolidine moiety not embedded in a polycyclic frame. The diverse synthetic approaches are classified according to the bond which is formed to complete the quaternary skeleton.

Entities:  

Year:  2008        PMID： 19655047      PMCID： PMC2719988          DOI： 10.1002/ejoc.200800225

Source DB:  PubMed          Journal:  European J Org Chem        ISSN： 1099-0690


  80 in total

Review 1.  The hunchback and its neighbours: proline as an environmental modulator.

Authors:  H Reiersen; A R Rees
Journal:  Trends Biochem Sci       Date:  2001-11       Impact factor: 13.807

2.  Total synthesis of kaitocephalin, the first naturally occurring AMPA/KA receptor antagonist.

Authors:  D Ma; J Yang
Journal:  J Am Chem Soc       Date:  2001-10-03       Impact factor: 15.419

3.  Application of a new chiral derivatizing agent to the enantioseparation of secondary amino acids.

Authors:  Antal Péter; Erika Vékes; Géza Tóth; Dirk Tourwé; Frans Borremans
Journal:  J Chromatogr A       Date:  2002-03-01       Impact factor: 4.759

Review 4.  Exploring Ramachandran and chi space: conformationally constrained amino acids and peptides in the design of bioactive polypeptide ligands.

Authors:  S M Cowell; Y S Lee; J P Cain; V J Hruby
Journal:  Curr Med Chem       Date:  2004-11       Impact factor: 4.530

5.  Construction of enantiopure pyrrolidine ring system via asymmetric [3+2]-cycloaddition of azomethine ylides.

Authors:  Ganesh Pandey; Prabal Banerjee; Smita R Gadre
Journal:  Chem Rev       Date:  2006-11       Impact factor: 60.622

6.  2,5-Disubstituted pyrrolidines: synthesis by enamine reduction and subsequent regioselective and diastereoselective alkylations.

Authors:  Syed Raziullah Hussaini; Mark G Moloney
Journal:  Org Biomol Chem       Date:  2006-05-31       Impact factor: 3.876

7.  Design of peptides, proteins, and peptidomimetics in chi space.

Authors:  V J Hruby; G Li; C Haskell-Luevano; M Shenderovich
Journal:  Biopolymers       Date:  1997       Impact factor: 2.505

8.  Synthesis, conformational properties, and antibody recognition of peptides containing beta-turn mimetics based on alpha-alkylproline derivatives.

Authors:  M G Hinds; J H Welsh; D M Brennand; J Fisher; M J Glennie; N G Richards; D L Turner; J A Robinson
Journal:  J Med Chem       Date:  1991-06       Impact factor: 7.446

9.  Membrane translocation mechanism of the antimicrobial peptide buforin 2.

Authors:  Satoe Kobayashi; Akinori Chikushi; Shiho Tougu; Yuichi Imura; Minoru Nishida; Yoshiaki Yano; Katsumi Matsuzaki
Journal:  Biochemistry       Date:  2004-12-14       Impact factor: 3.162

10.  Recoverable (R)- and (S)-binap-Ag(I) complexes for the enantioselective 1,3-dipolar cycloaddition reaction of azomethine ylides.

Authors:  Carmen Nájera; M de Gracia Retamosa; José M Sansano
Journal:  Org Lett       Date:  2007-09-08       Impact factor: 6.005
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  8 in total

1.  A straightforward route to enantiopure alpha-substituted derivatives of (2S,3aS,7aS)-octahydroindole-2-carboxylic acid.

Authors:  Francisco J Sayago; M Isabel Calaza; Ana I Jiménez; Carlos Cativiela
Journal:  Tetrahedron       Date:  2009-07-01       Impact factor: 2.457

2.  An analysis of the complementary stereoselective alkylations of imidazolidinone derivatives toward α-quaternary proline-based amino amides.

Authors:  Brian J Knight; Erin E Stache; Eric M Ferreira
Journal:  Tetrahedron       Date:  2015-05-09       Impact factor: 2.457

3.  Recent Progress on the Stereoselective Synthesis of Cyclic Quaternary alpha-Amino Acids.

Authors:  Carlos Cativiela; Mario Ordóñez
Journal:  Tetrahedron Asymmetry       Date:  2009-01-30

4.  Towards the stereoselective synthesis of alpha-methylated (2S,3aS,7aS)-octahydroindole-2-carboxylic acid.

Authors:  Francisco J Sayago; M Isabel Calaza; Ana I Jiménez; Carlos Cativiela
Journal:  Tetrahedron Asymmetry       Date:  2008-12-12

5.  Synthesis of Boc-protected bicycloproline.

Authors:  Sujeewa Ranatunga; Juan R Del Valle
Journal:  Tetrahedron Lett       Date:  2009-05-27       Impact factor: 2.415

6.  Lewis acid catalyzed [1,3]-sigmatropic rearrangement of vinyl aziridines.

Authors:  Matthew Brichacek; Dongeun Lee; Jon T Njardarson
Journal:  Org Lett       Date:  2008-10-09       Impact factor: 6.005

7.  Double nucleophilic addition to iminomalonate, leading to the synthesis of quaternary α-amino diesters and desymmetrization of the products.

Authors:  Makoto Shimizu; Miki Mushika; Isao Mizota; Yusong Zhu
Journal:  RSC Adv       Date:  2019-07-29       Impact factor: 4.036

8.  Ni(II)-catalyzed asymmetric alkenylations of ketimines.

Authors:  Mao Quan; Xiaoxiao Wang; Liang Wu; Ilya D Gridnev; Guoqiang Yang; Wanbin Zhang
Journal:  Nat Commun       Date:  2018-06-08       Impact factor: 14.919
  8 in total

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