Literature DB >> 27094932

Enantioselective, Stereodivergent Hydroazidation and Hydroamination of Allenes Catalyzed by Acyclic Diaminocarbene (ADC) Gold(I) Complexes.

Dimitri A Khrakovsky1, Chuanzhou Tao1,2, Miles W Johnson1,3, Richard T Thornbury1, Sophia L Shevick1, F Dean Toste4.   

Abstract

The gold-catalyzed enantioselective hydroazidation and hydroamination reactions of allenes are presented herein. ADC gold(I) catalysts derived from BINAM were critical for achieving high levels of enantioselectivity in both transformations. The sense of enantioinduction is reversed for the two different nucleophiles, allowing access to both enantiomers of the corresponding allylic amines using the same catalyst enantiomer.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  acyclic diaminocarbene; enantioselective synthesis; gold catalysis; hydroamination; hydroazidation

Mesh：

Substances：

Year:  2016        PMID： 27094932      PMCID： PMC4948301          DOI： 10.1002/anie.201601550

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


  34 in total

1.  Direct catalytic azidation of allylic alcohols.

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2.  New advances in dual stereocontrol for asymmetric reactions.

Authors:  Jorge Escorihuela; M Isabel Burguete; Santiago V Luis
Journal:  Chem Soc Rev       Date:  2013-06-21       Impact factor: 54.564

3.  Unlocking the N(2)  selectivity of benzotriazoles: regiodivergent and highly selective coupling of benzotriazoles with allenes.

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4.  Regio- and enantioselective synthesis of N-substituted pyrazoles by rhodium-catalyzed asymmetric addition to allenes.

Authors:  Alexander M Haydl; Kun Xu; Bernhard Breit
Journal:  Angew Chem Int Ed Engl       Date:  2015-04-29       Impact factor: 15.336

5.  Mechanistic study of gold(I)-catalyzed intermolecular hydroamination of allenes.

Authors:  Z Jane Wang; Diego Benitez; Ekaterina Tkatchouk; William A Goddard; F Dean Toste
Journal:  J Am Chem Soc       Date:  2010-09-22       Impact factor: 15.419

6.  Highly enantioselective conjugate additions to alpha,beta-unsaturated ketones catalyzed by a (salen)Al complex.

Authors:  Mark S Taylor; David N Zalatan; Andreas M Lerchner; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2005-02-02       Impact factor: 15.419

7.  Phosphoramidite gold(I)-catalyzed diastereo- and enantioselective synthesis of 3,4-substituted pyrrolidines.

Authors:  Ana Z González; Diego Benitez; Ekaterina Tkatchouk; William A Goddard; F Dean Toste
Journal:  J Am Chem Soc       Date:  2011-03-23       Impact factor: 15.419

8.  Rhodium-catalyzed chemo-, regio-, and enantioselective addition of 2-pyridones to terminal allenes.

Authors:  Changkun Li; Matthias Kähny; Bernhard Breit
Journal:  Angew Chem Int Ed Engl       Date:  2014-10-08       Impact factor: 15.336

9.  Enantioselective alkynylbenzaldehyde cyclizations catalyzed by chiral gold(I) acyclic diaminocarbene complexes containing weak Au-arene interactions.

Authors:  Sachin Handa; LeGrande M Slaughter
Journal:  Angew Chem Int Ed Engl       Date:  2012-01-04       Impact factor: 15.336

10.  Gold-catalyzed [4C+2C] cycloadditions of allenedienes, including an enantioselective version with new phosphoramidite-based catalysts: mechanistic aspects of the divergence between [4C+3C] and [4C+2C] pathways.

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Journal:  J Am Chem Soc       Date:  2009-09-16       Impact factor: 15.419
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  7 in total

Review 1.  Allylic azides: synthesis, reactivity, and the Winstein rearrangement.

Authors:  Angela S Carlson; Joseph J Topczewski
Journal:  Org Biomol Chem       Date:  2019-05-08       Impact factor: 3.876

2.  On the Winstein rearrangement: equilibrium and mechanism.

Authors:  Amy A Ott; Joseph J Topczewski
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3.  Reactivity of Diamines in Acyclic Diamino Carbene Gold Complexes.

Authors:  Guilherme M D M Rúbio; Tristan T Y Tan; Alexander Prado-Roller; Jia Min Chin; Michael R Reithofer
Journal:  Inorg Chem       Date:  2022-05-04       Impact factor: 5.436

4.  Enantioselective Synthesis of Trisubstituted Allenyl-B(pin) Compounds by Phosphine-Cu-Catalyzed 1,3-Enyne Hydroboration. Insights Regarding Stereochemical Integrity of Cu-Allenyl Intermediates.

Authors:  Youming Huang; Juan Del Pozo; Sebastian Torker; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2018-02-08       Impact factor: 15.419

5.  Chirality Transfer in Gold(I)-Catalysed Hydroalkoxylation of 1,3-Disubstituted Allenes.

Authors:  Stacey Webster; Daniel R Sutherland; Ai-Lan Lee
Journal:  Chemistry       Date:  2016-11-11       Impact factor: 5.236

6.  Divergent synthesis of chiral cyclic azides via asymmetric cycloaddition reactions of vinyl azides.

Authors:  Nuligonda Thirupathi; Fang Wei; Chen-Ho Tung; Zhenghu Xu
Journal:  Nat Commun       Date:  2019-07-18       Impact factor: 14.919

7.  Synthetically Versatile Nitrogen Acyclic Carbene Stabilized Gold Nanoparticles.

Authors:  Guilherme M D M Rúbio; Bernhard K Keppler; Jia Min Chin; Michael R Reithofer
Journal:  Chemistry       Date:  2020-11-18       Impact factor: 5.236
  7 in total

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