Literature DB >> 16791334

Catalytic asymmetric synthesis of alpha- and beta-amino phosphonic acid derivatives.

Jun-An Ma1.   

Abstract

Catalytic asymmetric reactions provide one of the most powerful and economical synthetic approaches to a variety of enantiomerically enriched compounds. As being analogues of the corresponding alpha- and beta-amino acids, optically active alpha- and beta-amino phosphonic acid derivatives have found widespread use in medicinal chemistry and the pharmaceutical sciences. Using catalytic amounts of chiral materials, asymmetric synthesis of enantiomerically enriched alpha- and beta-amino phosphonates has been a subject of growing interest. This tutorial review contains a compilation of the catalytic asymmetric synthetic methods developed to date and highlights their utility for obtaining these target compounds.

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Year:  2006        PMID: 16791334     DOI: 10.1039/b517100h

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  10 in total

1.  An Overview of Stereoselective Synthesis of α-Aminophosphonic Acids and Derivatives.

Authors:  Mario Ordóñez; Haydée Rojas-Cabrera; Carlos Cativiela
Journal:  Tetrahedron       Date:  2009-01-03       Impact factor: 2.457

2.  Synthesis and resolution of the biaryl-like diphosphine (S)-Me2-CATPHOS, preparation of a derived rhodium precatalyst and applications in asymmetric hydrogenation.

Authors:  Simon Doherty; Catherine H Smyth
Journal:  Nat Protoc       Date:  2012-09-20       Impact factor: 13.491

3.  Squaramide-catalyzed enantioselective Michael addition of diphenyl phosphite to nitroalkenes.

Authors:  Ye Zhu; Jeremiah P Malerich; Viresh H Rawal
Journal:  Angew Chem Int Ed Engl       Date:  2010       Impact factor: 15.336

4.  A novel approach to phosphonic acids from hypophosphorous acid.

Authors:  Karla Bravo-Altamirano; Jean-Luc Montchamp
Journal:  Tetrahedron Lett       Date:  2007-08-13       Impact factor: 2.415

5.  NHCs catalyzed hydrophosphonylation of α-ketoesters and α-trifluoromethyl ketones.

Authors:  Lin He; Zhi-Hua Cai; Ji-Xin Pian; Guang-Fen Du
Journal:  ScientificWorldJournal       Date:  2013-12-31

6.  Synthesis of Chiral Tertiary Boronic Esters: Phosphonate-Directed Catalytic Asymmetric Hydroboration of Trisubstituted Alkenes.

Authors:  Suman Chakrabarty; James M Takacs
Journal:  J Am Chem Soc       Date:  2017-04-20       Impact factor: 15.419

7.  Straightforward Synthesis of Bifunctional Phosphorus Phenols via Phosphination of In Situ Generated o-Quinone Methides.

Authors:  Zhangpei Chen; Qinglong Shi; Gongshu Wang; Siwen Chen; Jianshe Hu
Journal:  Molecules       Date:  2018-05-23       Impact factor: 4.411

Review 8.  Application of cyclic phosphonamide reagents in the total synthesis of natural products and biologically active molecules.

Authors:  Thilo Focken; Stephen Hanessian
Journal:  Beilstein J Org Chem       Date:  2014-08-13       Impact factor: 2.883

9.  Chiral expression from molecular to macroscopic level via pH modulation in terbium coordination polymers.

Authors:  Jian Huang; Hong-Ming Ding; Yan Xu; Dai Zeng; Hui Zhu; Dong-Mian Zang; Song-Song Bao; Yu-Qiang Ma; Li-Min Zheng
Journal:  Nat Commun       Date:  2017-12-14       Impact factor: 14.919

10.  1-(Acylamino)alkylphosphonic Acids-Alkaline Deacylation.

Authors:  Marek Cypryk; Jozef Drabowicz; Bartlomiej Gostynski; Marcin H Kudzin; Zbigniew H Kudzin; Pawel Urbaniak
Journal:  Molecules       Date:  2018-04-09       Impact factor: 4.411

  10 in total

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