Literature DB >> 12475318

Catalyzed asymmetric aryl transfer reactions to aldehydes with boronic acids as aryl source.

Carsten Bolm1, Jens Rudolph.   

Abstract

Chiral diaryl methanols are important intermediates for the synthesis of biologically active compounds. Here, we describe a flexible method for their catalyzed asymmetric synthesis from readily available starting materials. Noteworthy is the fact that with a single catalyst both enantiomers of the product are accessible simply by choosing the appropriate combination of aryl boronic acid or aldehyde as aryl donor and acceptor, respectively. The catalysis with a planar-chiral ferrocene is easy to perform and yields a broad range of products with excellent enantioselectivities (up to 98% ee).

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Year:  2002        PMID: 12475318     DOI: 10.1021/ja028518l

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


  14 in total

1.  A Chiral Nitrogen Ligand for Enantioselective, Iridium-Catalyzed Silylation of Aromatic C-H Bonds.

Authors:  Bo Su; Tai-Gang Zhou; Xian-Wei Li; Xiao-Ru Shao; Pei-Lin Xu; Wen-Lian Wu; John F Hartwig; Zhang-Jie Shi
Journal:  Angew Chem Int Ed Engl       Date:  2016-12-15       Impact factor: 15.336

2.  Rhodium-catalyzed enantioselective silylation of arene C-H bonds: desymmetrization of diarylmethanols.

Authors:  Taegyo Lee; Tyler W Wilson; Robert Berg; Per Ryberg; John F Hartwig
Journal:  J Am Chem Soc       Date:  2015-05-20       Impact factor: 15.419

3.  Asymmetric transition metal-catalyzed cross-coupling reactions for the construction of tertiary stereocenters.

Authors:  Elizabeth C Swift; Elizabeth R Jarvo
Journal:  Tetrahedron       Date:  2013-07-22       Impact factor: 2.457

4.  Selective synthesis of either enantiomer of an anti-breast cancer agent via a common enantioenriched intermediate.

Authors:  Aaron George Johnson; Marissa M Tranquilli; Michael R Harris; Elizabeth R Jarvo
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

5.  Continuous flow enantioselective arylation of aldehydes with ArZnEt using triarylboroxins as the ultimate source of aryl groups.

Authors:  Julien Rolland; Xacobe C Cambeiro; Carles Rodríguez-Escrich; Miquel A Pericàs
Journal:  Beilstein J Org Chem       Date:  2009-10-15       Impact factor: 2.883

6.  Nickel-catalyzed asymmetric cross-couplings of racemic propargylic halides with arylzinc reagents.

Authors:  Sean W Smith; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2008-09-03       Impact factor: 15.419

7.  Practical catalytic asymmetric synthesis of diaryl-, aryl heteroaryl-, and diheteroarylmethanols.

Authors:  Luca Salvi; Jeung Gon Kim; Patrick J Walsh
Journal:  J Am Chem Soc       Date:  2009-09-02       Impact factor: 15.419

8.  The catalytic asymmetric addition of alkyl- and aryl-zinc reagents to an isoxazole aldehyde.

Authors:  Jared K Nelson; Brendan Twamley; Trinidad J Villalobos; Nicholas R Natale
Journal:  Tetrahedron Lett       Date:  2008-10-06       Impact factor: 2.415

9.  Stereospecific nickel-catalyzed cross-coupling reactions of alkyl Grignard reagents and identification of selective anti-breast-cancer agents.

Authors:  Ivelina M Yonova; A George Johnson; Charlotte A Osborne; Curtis E Moore; Naomi S Morrissette; Elizabeth R Jarvo
Journal:  Angew Chem Int Ed Engl       Date:  2014-01-29       Impact factor: 15.336

10.  Functional-group-tolerant, nickel-catalyzed cross-coupling reaction for enantioselective construction of tertiary methyl-bearing stereocenters.

Authors:  Hanna M Wisniewska; Elizabeth C Swift; Elizabeth R Jarvo
Journal:  J Am Chem Soc       Date:  2013-06-10       Impact factor: 15.419

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