Literature DB >> 23495237

Chiral magnesium(II) binaphtholates as cooperative Brønsted/Lewis acid-base catalysts for the highly enantioselective addition of phosphorus nucleophiles to α,β-unsaturated esters and ketones.

Manabu Hatano1, Takahiro Horibe, Kazuaki Ishihara.   

Abstract

A little cooperation goes a long way: The cooperative Brønsted/Lewis acid-base supramolecular catalysts formed in situ from simple chiral magnesium(II) binaphtholate aqua complexes promoted the highly enantioselective 1,4-hydrophosphinylation of α,β-unsaturated esters with diaryl phosphine oxides and 1,2-hydrophosphonylation of α,β-unsaturated ketones with dialkyl phosphites (see scheme).
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2013        PMID: 23495237     DOI: 10.1002/anie.201300938

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  6 in total

1.  A Cooperative N-Heterocyclic Carbene/Palladium Catalysis System.

Authors:  Kun Liu; M Todd Hovey; Karl A Scheidt
Journal:  Chem Sci       Date:  2014-10-01       Impact factor: 9.825

Review 2.  s-Block Metal Catalysts for the Hydroboration of Unsaturated Bonds.

Authors:  Marc Magre; Marcin Szewczyk; Magnus Rueping
Journal:  Chem Rev       Date:  2022-03-07       Impact factor: 72.087

3.  NHCs catalyzed hydrophosphonylation of α-ketoesters and α-trifluoromethyl ketones.

Authors:  Lin He; Zhi-Hua Cai; Ji-Xin Pian; Guang-Fen Du
Journal:  ScientificWorldJournal       Date:  2013-12-31

4.  Brønsted acid catalyzed phosphoramidic acid additions to alkenes: diastereo- and enantioselective halogenative cyclizations for the synthesis of C- and P-chiral phosphoramidates.

Authors:  Yasunori Toda; Maren Pink; Jeffrey N Johnston
Journal:  J Am Chem Soc       Date:  2014-10-14       Impact factor: 15.419

5.  Nickel/Brønsted acid dual-catalyzed regio- and enantioselective hydrophosphinylation of 1,3-dienes: access to chiral allylic phosphine oxides.

Authors:  Jiao Long; Yuqiang Li; Weining Zhao; Guoyin Yin
Journal:  Chem Sci       Date:  2021-12-28       Impact factor: 9.825

6.  Synthesis of α,β-unsaturated esters via a chemo-enzymatic chain elongation approach by combining carboxylic acid reduction and Wittig reaction.

Authors:  Yitao Duan; Peiyuan Yao; Yuncheng Du; Jinhui Feng; Qiaqing Wu; Dunming Zhu
Journal:  Beilstein J Org Chem       Date:  2015-11-19       Impact factor: 2.883

  6 in total

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