Literature DB >> 10519909

Recent advances in the enantioselective synthesis of beta-amino acids.

E Juaristi1, H López-Ruiz.   

Abstract

The introductory section of this review presents some of the currently most compelling beta-amino acid targets, according to their structural types: alpha- and beta-aryl substituted, olefinic and alkynyl, alpha, alpha- and alpha,beta-disubstituted, cyclic and conformationally restricted, fluorine-containing, and phosphonic analogous beta-amino acids. The main section highlights some of the very new (1996-1998), promising methodology for the enantioselective synthesis of beta-amino acids, with especial emphasis on catalytic and enzymatic processes, as well as methods based on "chiral pool", self-regeneration of stereogenic centers , diastereoselective nucleophilic additions to prochiral double bonds, and enantioselective reactions in the presence of chiral additives.

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Year:  1999        PMID: 10519909

Source DB:  PubMed          Journal:  Curr Med Chem        ISSN: 0929-8673            Impact factor:   4.530


  9 in total

1.  Enantioselective radical reactions. Evaluation of nitrogen protecting groups in the synthesis of beta-amino acids.

Authors:  Mukund P Sibi; Kalyani Patil
Journal:  Tetrahedron Asymmetry       Date:  2006-02-20

2.  Enantioselective rhodium enolate protonations. A new methodology for the synthesis of beta2-amino acids.

Authors:  Mukund P Sibi; Hiroto Tatamidani; Kalyani Patil
Journal:  Org Lett       Date:  2005-06-23       Impact factor: 6.005

3.  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

4.  N-heterocyclic carbene-catalyzed enantioselective Mannich reactions with alpha-aryloxyacetaldehydes.

Authors:  Yasufumi Kawanaka; Eric M Phillips; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2009-12-23       Impact factor: 15.419

5.  Enantioselective hydrogenation of alpha-aminomethylacrylates containing a free NH group for the synthesis of beta-amino acid derivatives.

Authors:  Liqin Qiu; Mahavir Prashad; Bin Hu; Kapa Prasad; Oljan Repic; Thomas J Blacklock; Fuk Yee Kwong; Stanton H L Kok; Hang Wai Lee; Albert S C Chan
Journal:  Proc Natl Acad Sci U S A       Date:  2007-10-17       Impact factor: 11.205

6.  Potential application of N-carbamoyl-beta-alanine amidohydrolase from Agrobacterium tumefaciens C58 for beta-amino acid production.

Authors:  Ana Isabel Martínez-Gómez; Sergio Martínez-Rodríguez; Joaquín Pozo-Dengra; Davide Tessaro; Stefano Servi; Josefa María Clemente-Jiménez; Felipe Rodríguez-Vico; Francisco Javier Las Heras-Vázquez
Journal:  Appl Environ Microbiol       Date:  2008-11-14       Impact factor: 4.792

7.  Direct enzymatic route for the preparation of novel enantiomerically enriched hydroxylated beta-amino ester stereoisomers.

Authors:  Eniko Forró; László Schönstein; Loránd Kiss; Alberto Vega-Peñaloza; Eusebio Juaristi; Ferenc Fülöp
Journal:  Molecules       Date:  2010-06-01       Impact factor: 4.411

8.  Mechanochemical enzymatic resolution of N-benzylated-β3-amino esters.

Authors:  Mario Pérez-Venegas; Gloria Reyes-Rangel; Adrián Neri; Jaime Escalante; Eusebio Juaristi
Journal:  Beilstein J Org Chem       Date:  2017-08-18       Impact factor: 2.883

9.  Enantioselective catalytic β-amination through proton-coupled electron transfer followed by stereocontrolled radical-radical coupling.

Authors:  Zijun Zhou; Yanjun Li; Bowen Han; Lei Gong; Eric Meggers
Journal:  Chem Sci       Date:  2017-06-15       Impact factor: 9.825

  9 in total

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