Literature DB >> 18315002

Acceleration of arylzinc formation and its enantioselective addition to aldehydes by microwave irradiation and aziridine-2-methanol catalysts.

Antonio L Braga1, Marcio W Paixão, Bernhard Westermann, Paulo H Schneider, Ludger A Wessjohann.   

Abstract

The formation and 2-amino alcohol catalyzed addition of arylzinc reagents from and with boronic acids, respectively, is drastically accelerated to a few minutes under microwave irradiation without loss of enantioselectivity (up to 98% ee). Of the amino acid derived catalysts tested, the conformationally restricted bulky substituted aziridine-2-methanols derived from serine show the best overall performance in the formation of diarylmethanols.

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Year:  2008        PMID： 18315002     DOI： 10.1021/jo702413n

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


  10 in total

Review 1.  Controlled microwave heating in modern organic synthesis: highlights from the 2004-2008 literature.

Authors:  C Oliver Kappe; Doris Dallinger
Journal:  Mol Divers       Date:  2009-04-21       Impact factor: 2.943

2.  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

3.  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

4.  Synthesis of Triarylmethanes via Palladium-Catalyzed Suzuki-Miyaura Reactions of Diarylmethyl Esters.

Authors:  Amira H Dardir; Irene Casademont-Reig; David Balcells; Jonathan D Ellefsen; Matthew R Espinosa; Nilay Hazari; Nicholas E Smith
Journal:  Organometallics       Date:  2021-05-27       Impact factor: 3.837

5.  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

6.  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

7.  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

8.  Catalytic enantioselective aryl transfer to aldehydes using chiral 2,2'-bispyrrolidine-based salan ligands.

Authors:  Xuefeng Jia; Aijun Lin; Zhijie Mao; Chengjian Zhu; Yixiang Cheng
Journal:  Molecules       Date:  2011-04-06       Impact factor: 4.411

9.  Optically Pure Aziridin-2-yl Methanols as Readily Available 1H NMR Sensors for Enantiodiscrimination of α-Racemic Carboxylic Acids Containing Tertiary or Quaternary Stereogenic Centers.

Authors:  Martyna Malinowska; Szymon Jarzyński; Adam Pieczonka; Michał Rachwalski; Stanisław Leśniak; Anna Zawisza
Journal:  J Org Chem       Date:  2020-09-02       Impact factor: 4.354

10.  Harnessing C-O Bonds in Stereoselective Cross-Coupling and Cross-Electrophile Coupling Reactions.

Authors:  Amberly B Sanford; Elizabeth R Jarvo
Journal:  Synlett       Date:  2020-11-27       Impact factor: 2.454
  10 in total

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