Literature DB >> 12465962

Highly enantioselective rhodium-catalyzed hydrogenation of beta-dehydroamino acid derivatives using monodentate phosphoramidites.

Diego Peña1, Adriaan J Minnaard, Johannes G De Vries, Ben L Feringa.   

Abstract

New and very easily accessible monodentate phosphoramidite ligands have been developed that lead to excellent ee's and full conversions in the hydrogenation of (E)- and (Z)-beta-dehydroamino acid derivatives with both aliphatic and aromatic side chains. Particularly, two different catalytic systems were established for (E)-beta-(acylamino)acrylates (98-99% ee) and (Z)-beta-(acylamino)acrylates (92-95% ee) based on phosphoramidites 2 and 3, respectively.

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Year:  2002        PMID： 12465962     DOI： 10.1021/ja028235t

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


  9 in total

1.  A combinatorial approach to the identification of self-assembled ligands for rhodium-catalysed asymmetric hydrogenation.

Authors:  Joerg Wieland; Bernhard Breit
Journal:  Nat Chem       Date:  2010-08-22       Impact factor: 24.427

2.  (R)-2,2'-BINAPHTHOYL-(S,S)-DI(1-PHENYLETHYL) AMINOPHOSPHINE. SCALABLE PROTOCOLS FOR THE SYNTHESES OF PHOSPHORAMIDITE (FERINGA) LIGANDS.

Authors:  Craig R Smith; Daniel J Mans; T V Rajanbabu; Scott E Denmark; Son T Nguyen
Journal:  Organic Synth       Date:  2008

Review 3.  Dehydroamino acids: chemical multi-tools for late-stage diversification.

Authors:  Jonathan W Bogart; Albert A Bowers
Journal:  Org Biomol Chem       Date:  2019-04-10       Impact factor: 3.876

4.  Ligand scaffold optimization of a supramolecular hydrogenation catalyst: Analyzing the influence of key structural subunits on reactivity and selectivity.

Authors:  Nathan C Thacker; Shin A Moteki; James M Takacs
Journal:  ACS Catal       Date:  2012-11-05       Impact factor: 13.084

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.  Remarkably diastereoselective synthesis of a chiral biphenyl diphosphine ligand and its application in asymmetric hydrogenation.

Authors:  Liqin Qiu; Jing Wu; Shusun Chan; Terry T-L Au-Yeung; Jian-Xin Ji; Rongwei Guo; Cheng-Chao Pai; Zhongyuan Zhou; Xingshu Li; Qing-Hua Fan; Albert S C Chan
Journal:  Proc Natl Acad Sci U S A       Date:  2004-04-05       Impact factor: 11.205

7.  New biphenol-based, fine-tunable monodentate phosphoramidite ligands for catalytic asymmetric transformations.

Authors:  Zihao Hua; Victor C Vassar; Hojae Choi; Iwao Ojima
Journal:  Proc Natl Acad Sci U S A       Date:  2004-03-12       Impact factor: 11.205

8.  Synthesis and characterization of privileged monodentate phosphoramidite ligands and chiral Brønsted acids derived from d-mannitol.

Authors:  Abdullah Mohammed A Al-Majid; Assem Barakat; Yahia Nasser Mabkhot; Mohammad Shahidul Islam
Journal:  Int J Mol Sci       Date:  2012-02-29       Impact factor: 6.208

9.  Synthesis of N-aryl β-amino acid derivatives via Cu(ii)-catalyzed asymmetric 1,4-reduction in air.

Authors:  Min Li; Hong-Feng Xia; Li-Yao Yang; Tao Hong; Lin-Jie Xie; Shijun Li; Jing Wu
Journal:  RSC Adv       Date:  2019-03-20       Impact factor: 4.036
  9 in total

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