Literature DB >> 16805561

TADDOL-derived phosphites and phosphoramidites for efficient rhodium-catalyzed asymmetric hydroboration.

Shin A Moteki1, Di Wu, Kusum L Chandra, D Sahadeva Reddy, James M Takacs.   

Abstract

[reaction: see text] Two simple TADDOL-derived monodentate ligands, the (1R,2S)-2-phenylcyclohexanol-derived phosphite and the N,N-(phenylbenzyl)phosphoramidite, give comparably high levels of enantioselectivity (90-96% ee) in the rhodium-catalyzed hydroborations of substituted styrenes bearing either electron-donating or electron-withdrawing substituents. Rhodium(I) chloride and tetrafluoroborate catalyst precursors give comparable results. Pinacolborane is superior to catecholborane in these reactions.

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Year:  2006        PMID: 16805561     DOI: 10.1021/ol061117g

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  6 in total

1.  γ-Selective directed catalytic asymmetric hydroboration of 1,1-disubstituted alkenes.

Authors:  Sean M Smith; Gia L Hoang; Rhitankar Pal; Mohammad O Bani Khaled; Liberty S W Pelter; Xiao Cheng Zeng; James M Takacs
Journal:  Chem Commun (Camb)       Date:  2012-12-28       Impact factor: 6.222

2.  Remarkable levels of enantioswitching in catalytic asymmetric hydroboration.

Authors:  Sean M Smith; James M Takacs
Journal:  Org Lett       Date:  2010-10-15       Impact factor: 6.005

3.  Surprisingly Facile C-H Activation in the Course of Oxime-Directed Catalytic Asymmetric Hydroboration.

Authors:  Nathan C Thacker; Veronika M Shoba; Andrew E Geis; James M Takacs
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

4.  Amide-directed catalytic asymmetric hydroboration of trisubstituted alkenes.

Authors:  Sean M Smith; James M Takacs
Journal:  J Am Chem Soc       Date:  2010-02-17       Impact factor: 15.419

5.  Synthesis of Chiral Tertiary Boronic Esters by Oxime-Directed Catalytic Asymmetric Hydroboration.

Authors:  Veronika M Shoba; Nathan C Thacker; Andrew J Bochat; James M Takacs
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-10       Impact factor: 15.336

6.  Arylation of Axially Chiral Phosphorothioate Salts by Dinuclear PdI Catalysis.

Authors:  Xiang-Yu Chen; Maoping Pu; Hong-Gang Cheng; Theresa Sperger; Franziska Schoenebeck
Journal:  Angew Chem Int Ed Engl       Date:  2019-07-09       Impact factor: 15.336

  6 in total

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