Literature DB >> 23956126

Rhodium-catalyzed dynamic kinetic asymmetric transformations of racemic allenes by the [3+2] annulation of aryl ketimines.

Duc N Tran1, Nicolai Cramer.   

Abstract

Racemization required: Rhodium(I)-catalyzed C-H activation directed by unprotected ketimines initiates selective [3+2] cycloaddition with allenes, providing access to highly substituted indenylamines. The reaction proceeds through the dynamic kinetic asymmetric transformation of racemic allenes. The catalyst controls the enantio- and diastereoselectivity, the regioselectivities of the C-H activation and allene incorporation, as well as the E/Z ratio.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  CH activation; DYKAT; allenes; asymmetric catalysis; rhodium

Mesh:

Substances:

Year:  2013        PMID: 23956126     DOI: 10.1002/anie.201304919

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


  12 in total

1.  Advances in Stereoconvergent Catalysis from 2005 to 2015: Transition-Metal-Mediated Stereoablative Reactions, Dynamic Kinetic Resolutions, and Dynamic Kinetic Asymmetric Transformations.

Authors:  Vikram Bhat; Eric R Welin; Xuelei Guo; Brian M Stoltz
Journal:  Chem Rev       Date:  2017-02-06       Impact factor: 60.622

2.  Iron-Catalyzed Contrasteric Functionalization of Allenic C(sp2)-H Bonds: Synthesis of α-Aminoalkyl 1,1-Disubstituted Allenes.

Authors:  Yidong Wang; Sarah G Scrivener; Xiao-Dong Zuo; Ruihan Wang; Philip N Palermo; Ethan Murphy; Austin C Durham; Yi-Ming Wang
Journal:  J Am Chem Soc       Date:  2021-09-07       Impact factor: 16.383

3.  Enantioselective nickel-catalyzed arylative and alkenylative intramolecular 1,2-allylations of tethered allene-ketones.

Authors:  Riccardo Di Sanza; Thi Le Nhon Nguyen; Naeem Iqbal; Stephen P Argent; William Lewis; Hon Wai Lam
Journal:  Chem Sci       Date:  2020-01-21       Impact factor: 9.825

4.  Asymmetric synthesis of N-allylic indoles via regio- and enantioselective allylation of aryl hydrazines.

Authors:  Kun Xu; Thomas Gilles; Bernhard Breit
Journal:  Nat Commun       Date:  2015-07-03       Impact factor: 14.919

5.  Enantioselective Generation of Adjacent Stereocenters in a Copper-Catalyzed Three-Component Coupling of Imines, Allenes, and Diboranes.

Authors:  Kay Yeung; Rebecca E Ruscoe; James Rae; Alexander P Pulis; David J Procter
Journal:  Angew Chem Int Ed Engl       Date:  2016-08-19       Impact factor: 15.336

6.  Rhodium(i)-catalyzed stereoselective [4+2] cycloaddition of oxetanols with alkynes through C(sp3)-C(sp3) bond cleavage.

Authors:  Rui Guo; Xinxin Zheng; Dayong Zhang; Guozhu Zhang
Journal:  Chem Sci       Date:  2017-01-23       Impact factor: 9.825

7.  Palladium-Catalyzed, Enantioselective Formal Cycloaddition between Benzyltriflamides and Allenes: Straightforward Access to Enantioenriched Isoquinolines.

Authors:  Xandro Vidal; José L Mascareñas; Moisés Gulías
Journal:  J Am Chem Soc       Date:  2019-01-22       Impact factor: 15.419

8.  Copper-Catalyzed Borylative Cross-Coupling of Allenes and Imines: Selective Three-Component Assembly of Branched Homoallyl Amines.

Authors:  James Rae; Kay Yeung; Joseph J W McDouall; David J Procter
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-03       Impact factor: 15.336

9.  Enantioselective Rhodium-Catalyzed Coupling of Arylboronic Acids, 1,3-Enynes, and Imines by Alkenyl-to-Allyl 1,4-Rhodium(I) Migration.

Authors:  Michael Callingham; Benjamin M Partridge; William Lewis; Hon Wai Lam
Journal:  Angew Chem Int Ed Engl       Date:  2017-11-24       Impact factor: 15.336

10.  Pivalophenone imine as a benzonitrile surrogate for directed C-H bond functionalization.

Authors:  Wengang Xu; Naohiko Yoshikai
Journal:  Chem Sci       Date:  2017-05-30       Impact factor: 9.825

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