Literature DB >> 23297694

Diametric stereocontrol in dynamic catalytic reduction of racemic acyl phosphonates: divergence from α-keto ester congeners.

Michael T Corbett1, Jeffrey S Johnson.   

Abstract

An unexpected dichotomy was observed in the Ru-catalyzed asymmetric transfer hydrogenation of acyl phosphonates: reduction proceeded from the opposite face relative to that observed in the analogous reduction of α-keto esters. The first highly selective catalytic hydrogenation of acyl phosphonates was utilized in the dynamic kinetic resolution of α-aryl acyl phosphonates, providing β-stereogenic α-hydroxy phosphonic acid derivatives.

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Year:  2013        PMID： 23297694      PMCID： PMC3552383          DOI： 10.1021/ja310980q

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


  34 in total

1.  Design of chiral ligands for asymmetric catalysis: from C2-symmetric P,P- and N,N-ligands to sterically and electronically nonsymmetrical P,N-ligands.

Authors:  Andreas Pfaltz; William J Drury
Journal:  Proc Natl Acad Sci U S A       Date:  2004-04-06       Impact factor: 11.205

2.  Dynamic kinetic resolution of α-keto esters via asymmetric transfer hydrogenation.

Authors:  Kimberly M Steward; Emily C Gentry; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2012-04-17       Impact factor: 15.419

3.  Synthesis of an optically active C1-symmetric Al(salalen) complex and its application to the catalytic hydrophosphonylation of aldehydes.

Authors:  Bunnai Saito; Tsutomu Katsuki
Journal:  Angew Chem Int Ed Engl       Date:  2005-07-18       Impact factor: 15.336

4.  Catalytic Asymmetric Synthesis of alpha-Hydroxy Phosphonates Using the Al-Li-BINOL Complex.

Authors:  Takayoshi Arai; Masahiro Bougauchi; Hiroaki Sasai; Masakatsu Shibasaki
Journal:  J Org Chem       Date:  1996-05-03       Impact factor: 4.354

5.  Small-molecule catalysis.

Authors:  Andrew Mitchinson; Joshua Finkelstein
Journal:  Nature       Date:  2008-09-18       Impact factor: 49.962

6.  Organocatalytic High Enantioselective Synthesis of β-Formyl-α-hydroxyphosphonates.

Authors:  Sandun Perera; Vijaya Kumar Naganaboina; Long Wang; Bin Zhang; Qunsheng Guo; Laxmidhar Rout; Cong-Gui Zhao
Journal:  Adv Synth Catal       Date:  2011-06-30       Impact factor: 5.837

7.  Highly enantioselective hydrogenation of enol ester phosphonates catalyzed by rhodium phosphine-phosphite complexes.

Authors:  Miguel Rubio; Andrés Suárez; Eleuterio Alvarez; Antonio Pizzano
Journal:  Chem Commun (Camb)       Date:  2004-12-10       Impact factor: 6.222

8.  alpha-Hydroxy phosphinyl-based inhibitors of human renin.

Authors:  D V Patel; K Rielly-Gauvin; D E Ryono; C A Free; W L Rogers; S A Smith; J M DeForrest; R S Oehl; E W Petrillo
Journal:  J Med Chem       Date:  1995-10-27       Impact factor: 7.446

9.  Enantioselective Friedel-Crafts alkylations catalyzed by bis(oxazolinyl)pyridine-scandium(III) triflate complexes.

Authors:  David A Evans; Keith R Fandrick; Hyun-Ji Song; Karl A Scheidt; Risheng Xu
Journal:  J Am Chem Soc       Date:  2007-07-21       Impact factor: 15.419

10.  Generation of chiral phosphonium dialkyl phosphite as a highly reactive P-nucleophile: application to asymmetric hydrophosphonylation of aldehydes.

Authors:  Daisuke Uraguchi; Takaki Ito; Takashi Ooi
Journal:  J Am Chem Soc       Date:  2009-03-25       Impact factor: 15.419
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  8 in total

1.  Synthesis of Complex Glycolates by Enantioconvergent Addition Reactions.

Authors:  Samuel L Bartlett; Jeffrey S Johnson
Journal:  Acc Chem Res       Date:  2017-08-17       Impact factor: 22.384

2.  Advances in Stereoconvergent Catalysis from 2005 to 2015: Transition-Metal-Mediated Stereoablative Reactions, Dynamic Kinetic Resolutions, and Dynamic Kinetic Asymmetric Transformations.

Authors:  Vikram Bhat; Eric R Welin; Xuelei Guo; Brian M Stoltz
Journal:  Chem Rev       Date:  2017-02-06       Impact factor: 60.622

3.  Synthesis of Complex Tertiary Glycolates by Enantioconvergent Arylation of Stereochemically Labile α-Keto Esters.

Authors:  Samuel L Bartlett; Kimberly M Keiter; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2017-03-02       Impact factor: 15.419

4.  Asymmetric homoenolate additions to acyl phosphonates through rational design of a tailored N-heterocyclic carbene catalyst.

Authors:  Ki Po Jang; Gerri E Hutson; Ryne C Johnston; Elizabeth O McCusker; Paul H-Y Cheong; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2013-12-17       Impact factor: 15.419

5.  Asymmetric synthesis of anti-β-amino-α-hydroxy esters via dynamic kinetic resolution of β-amino-α-keto esters.

Authors:  C Guy Goodman; Dung T Do; Jeffrey S Johnson
Journal:  Org Lett       Date:  2013-04-30       Impact factor: 6.005

6.  Dynamic kinetic asymmetric transformations of β-stereogenic α-ketoesters by direct aldolization.

Authors:  Michael T Corbett; Jeffrey S Johnson
Journal:  Angew Chem Int Ed Engl       Date:  2013-11-12       Impact factor: 15.336

7.  Dynamic kinetic asymmetric cross-benzoin additions of β-stereogenic α-keto esters.

Authors:  C Guy Goodman; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2014-10-09       Impact factor: 15.419

8.  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
  8 in total

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