Literature DB >> 14629176

High efficiency and enantioselectivity in the rh-catalyzed conjugate addition of arylboronic acids using monodentate phosphoramidites.

Jean-Guy Boiteau1, Adriaan J Minnaard, Ben L Feringa.   

Abstract

A very fast reaction and enantioselectivities >98% have been reached in the rhodium-catalyzed arylboronic acid addition to enones using a monodentate phosphoramidite ligand. Temperature-dependent studies show that monodentate phosphoramidites form stable complexes with metals and can induce high enantioselectivities even at high temperatures in polar solvents.

Entities:  

Year:  2003        PMID: 14629176     DOI: 10.1021/jo035155e

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  3 in total

1.  (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

2.  Desymmetrization of enone-diones via rhodium-catalyzed diastereo- and enantioselective tandem conjugate addition-aldol cyclization.

Authors:  Brian M Bocknack; Long-Cheng Wang; Michael J Krische
Journal:  Proc Natl Acad Sci U S A       Date:  2004-03-15       Impact factor: 11.205

3.  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

  3 in total

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