Literature DB >> 16117520

An air-stable P-chiral phosphine ligand for highly enantioselective transition-metal-catalyzed reactions.

Tsuneo Imamoto1, Keitaro Sugita, Kazuhiro Yoshida.   

Abstract

A new P-chiral phosphine ligand, (R,R)-2,3-bis(tert-butylmethylphosphino)quinoxaline, has been prepared by the reaction of enantiomerically pure tert-butylmethylphosphine-borane with 2,3-dichloroquinoxaline. This ligand, in contrast to most of the previously reported P-chiral ligands, is an air-stable solid and exhibits excellent enantioselectivities in both Rh-catalyzed asymmetric hydrogenations and Rh- or Pd-catalyzed carbon-carbon bond-forming reactions.

Entities:  

Year:  2005        PMID: 16117520     DOI: 10.1021/ja053458f

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


  9 in total

1.  Pd-catalyzed enantioselective allyl-allyl cross-coupling.

Authors:  Ping Zhang; Laura A Brozek; James P Morken
Journal:  J Am Chem Soc       Date:  2010-08-11       Impact factor: 15.419

2.  Diastereocontrol in asymmetric allyl-allyl cross-coupling: stereocontrolled reaction of prochiral allylboronates with prochiral allyl chlorides.

Authors:  Laura A Brozek; Michael J Ardolino; James P Morken
Journal:  J Am Chem Soc       Date:  2011-10-05       Impact factor: 15.419

3.  Catalytic enantioselective allyl-allyl cross-coupling with a borylated allylboronate.

Authors:  Hai Le; Robert E Kyne; Laura A Brozek; James P Morken
Journal:  Org Lett       Date:  2013-03-19       Impact factor: 6.005

4.  Pd(OAc)2-catalyzed asymmetric hydrogenation of sterically hindered N-tosylimines.

Authors:  Jianzhong Chen; Zhenfeng Zhang; Bowen Li; Feilong Li; Yulin Wang; Min Zhao; Ilya D Gridnev; Tsuneo Imamoto; Wanbin Zhang
Journal:  Nat Commun       Date:  2018-11-27       Impact factor: 14.919

Review 5.  Synthesis and applications of high-performance P-chiral phosphine ligands.

Authors:  Tsuneo Imamoto
Journal:  Proc Jpn Acad Ser B Phys Biol Sci       Date:  2021       Impact factor: 3.493

Review 6.  Preparation of phosphines through C-P bond formation.

Authors:  Iris Wauters; Wouter Debrouwer; Christian V Stevens
Journal:  Beilstein J Org Chem       Date:  2014-05-09       Impact factor: 2.883

7.  Regioselective palladium-catalyzed ring-opening reactions of C1-substituted oxabicyclo[2,2,1]hepta-2,5-diene-2,3-dicarboxylates.

Authors:  Michael Edmunds; Mohammed Abdul Raheem; Rebecca Boutin; Katrina Tait; William Tam
Journal:  Beilstein J Org Chem       Date:  2016-02-09       Impact factor: 2.883

8.  Computational design of high-performance ligand for enantioselective Markovnikov hydroboration of aliphatic terminal alkenes.

Authors:  Hiroaki Iwamoto; Tsuneo Imamoto; Hajime Ito
Journal:  Nat Commun       Date:  2018-06-12       Impact factor: 14.919

9.  An N-linked bidentate phosphoramidite ligand (N-Me-BIPAM) for rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated ketones.

Authors:  Yasunori Yamamoto; Kazunori Kurihara; Yoshinori Takahashi; Norio Miyaura
Journal:  Molecules       Date:  2012-12-20       Impact factor: 4.411

  9 in total

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