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Literature DB >> 15024119

Asymmetric hydrogenation of alpha,beta-unsaturated phosphonates with Rh-BisP* and Rh-MiniPHOS catalysts: scope and mechanism of the reaction.

Ilya D Gridnev¹, Masaya Yasutake, Tsuneo Imamoto, Irina P Beletskaya.

Abstract

Optically active 1,2-bis(alkylmethylphosphino)ethanes and bis(alkylmethylphosphino)methanes are unique diphosphine ligands combining the simple molecular structure and P-stereogenic asymmetric environment. This work shows that these ligands exhibit excellent enantioselectivity in rhodium-catalyzed asymmetric hydrogenation of alpha,beta-unsaturated phosphonic acid derivatives. The enantioselective hydrogenation mechanism elucidated by NMR study is also described.

Entities: Chemical

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Year: 2004 PMID： 15024119 PMCID： PMC397390 DOI： 10.1073/pnas.0306993101

Source DB: PubMed Journal: Proc Natl Acad Sci U S A ISSN： 0027-8424 Impact factor: 11.205

13 in total

1. Methylene-Bridged P-Chiral Diphosphines in Highly Enantioselective Reactions.

Authors: Yoshinori Yamanoi; Tsuneo Imamoto
Journal: J Org Chem Date: 1999-04-30 Impact factor: 4.354

2. A Simple Model for the Origin of Enantioselection and the Anti "Lock-and-Key" Motif in Asymmetric Hydrogenation of Enamides as Catalyzed by Chiral Diphosphine Complexes of Rh(I) This work was supported by the National Science Foundation (CHE-9618497) and by the National Center for Supercomputer Applications under MCA99S017N and used the CRAY ORIGIN 2000 computer system at the NCSA.

Authors:
Journal: Angew Chem Int Ed Engl Date: 2000-08-18 Impact factor: 15.336

3. 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

4. 2-Amino-4-phosphonobutyric acid as a glutamate antagonist on locust muscle.

Authors: S G Cull-Candy; J F Donnellan; R W James; G G Lunt
Journal: Nature Date: 1976-07-29 Impact factor: 49.962

5. Highly enantioselective hydrogenation of (E)-beta-(acylamino)acrylates catalyzed by Rh(i)-complexes of electron-rich P-chirogenic diphosphines.

Authors: M Yasutake; I D Gridnev; N Higashi; T Imamoto
Journal: Org Lett Date: 2001-05-31 Impact factor: 6.005

6. Phosphonopeptides, a new class of synthetic antibacterial agents.

Authors: J G Allen; F R Atherton; M J Hall; C H Hassall; S W Holmes; R W Lambert; L J Nisbet; P S Ringrose
Journal: Nature Date: 1978-03-02 Impact factor: 49.962

7. Studies on phosphonic acid antibiotics. IV. Synthesis and antibacterial activity of analogs of 3-(N-acetyl-N-hydroxyamino)-propylphosphonic acid (FR-900098).

Authors: K Hemmi; H Takeno; M Hashimoto; T Kamiya
Journal: Chem Pharm Bull (Tokyo) Date: 1982-01 Impact factor: 1.645

8. Synthesis and structure-activity relationships of antibacterial phosphonopeptides incorporating (1-aminoethyl)phosphonic acid and (aminomethyl)phosphonic acid.

Authors: F R Atherton; C H Hassall; R W Lambert
Journal: J Med Chem Date: 1986-01 Impact factor: 7.446

Asymmetric hydrogenation of alpha,beta-unsaturated phosphonates with Rh-BisP* and Rh-MiniPHOS catalysts: scope and mechanism of the reaction.

1. Methylene-Bridged P-Chiral Diphosphines in Highly Enantioselective Reactions.

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

4. 2-Amino-4-phosphonobutyric acid as a glutamate antagonist on locust muscle.

5. Highly enantioselective hydrogenation of (E)-beta-(acylamino)acrylates catalyzed by Rh(i)-complexes of electron-rich P-chirogenic diphosphines.

6. Phosphonopeptides, a new class of synthetic antibacterial agents.

7. Studies on phosphonic acid antibiotics. IV. Synthesis and antibacterial activity of analogs of 3-(N-acetyl-N-hydroxyamino)-propylphosphonic acid (FR-900098).

8. Synthesis and structure-activity relationships of antibacterial phosphonopeptides incorporating (1-aminoethyl)phosphonic acid and (aminomethyl)phosphonic acid.

9. Phosphonopeptides as antibacterial agents: mechanism of action of alaphosphin.

10. Synthesis of novel N-phosphonoalkyl dipeptide inhibitors of human collagenase.

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

Review 2. Synthesis and applications of high-performance P-chiral phosphine ligands.

3. Trimerization and cyclization of reactive P-functionalities confined within OCO pincers.