Literature DB >> 30740841

Dynamic Kinetic Resolution of Aldehydes by Hydroacylation.

Zhiwei Chen1, Yusuke Aota1,2, Hillary M H Nguyen1, Vy M Dong1.   

Abstract

We report a dynamic kinetic resolution (DKR) of chiral 4-pentenals by olefin hydroacylation. A primary amine racemizes the aldehyde substrate via enamine formation and hydrolysis. Then, a cationic rhodium catalyst promotes hydroacylation to generate α,γ-disubstituted cyclopentanones with high enantio- and diastereoselectivities.
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−H activation; dual catalysis; dynamic kinetic resolution; hydroacylation; rhodium

Mesh：

Substances：

Year:  2019        PMID： 30740841      PMCID： PMC6501835          DOI： 10.1002/anie.201900545

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


  35 in total

1.  A Highly Active Catalyst System for Intermolecular Hydroacylation This work was supported by the Brain Korea 21 Project.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-09-01       Impact factor: 15.336

2.  Combination of enzymes and metal catalysts. A powerful approach in asymmetric catalysis.

Authors:  Oscar Pàmies; Jan-E Bäckvall
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

Review 3.  Concurrent tandem catalysis.

Authors:  Julia-Christina Wasilke; Stephen J Obrey; R Tom Baker; Guillermo C Bazan
Journal:  Chem Rev       Date:  2005-03       Impact factor: 60.622

4.  Ru-catalyzed asymmetric hydrogenation of racemic aldehydes via dynamic kinetic resolution: efficient synthesis of optically active primary alcohols.

Authors:  Jian-Hua Xie; Zhang-Tao Zhou; Wei-Ling Kong; Qi-Lin Zhou
Journal:  J Am Chem Soc       Date:  2007-01-31       Impact factor: 15.419

5.  Dynamic kinetic resolution via asymmetric conjugate reduction: enantio- and diastereoselective synthesis of 2,4-dialkyl cyclopentanones.

Authors:  Valdas Jurkauskas; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2002-03-27       Impact factor: 15.419

6.  Catalytic asymmetric reductive amination of aldehydes via dynamic kinetic resolution.

Authors:  Sebastian Hoffmann; Marcello Nicoletti; Benjamin List
Journal:  J Am Chem Soc       Date:  2006-10-11       Impact factor: 15.419

7.  Enantioselective alkylation of acyclic alpha,alpha-disubstituted tributyltin enolates catalyzed by a {Cr(salen)} complex.

Authors:  Abigail G Doyle; Eric N Jacobsen
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

8.  Concurrent induction of two chiral centers from symmetrical 3, 4-disubstituted and 3,3,4-trisubstituted 4-pentenals using Rh-catalyzed asymmetric cyclizations

Authors: 
Journal:  J Org Chem       Date:  2000-09-08       Impact factor: 4.354

9.  Parallel kinetic resolution of 4-alkynals catalyzed by Rh(I)/Tol-BINAP: synthesis of enantioenriched cyclobutanones and cyclopentenones.

Authors:  Ken Tanaka; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2003-07-09       Impact factor: 15.419

10.  Enantioselective synthesis of cyclopentenones via rhodium-catalyzed kinetic resolution and desymmetrization of 4-alkynals.

Authors:  Ken Tanaka; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2002-09-04       Impact factor: 15.419
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  2 in total

Review 1.  Teaching Aldehydes New Tricks Using Rhodium- and Cobalt-Hydride Catalysis.

Authors:  Ryan T Davison; Erin L Kuker; Vy M Dong
Journal:  Acc Chem Res       Date:  2021-02-03       Impact factor: 22.384

2.  [3+2] Cycloaddition of alkyl aldehydes and alkynes enabled by photoinduced hydrogen atom transfer.

Authors:  Siya Le; Ji Li; Jian Feng; Zuxiao Zhang; Yihui Bai; Zheliang Yuan; Gangguo Zhu
Journal:  Nat Commun       Date:  2022-08-12       Impact factor: 17.694
  2 in total

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