Literature DB >> 27134619

Rhodium(I)-Catalyzed Intermolecular Hydroacylation of α-Keto Amides and Isatins with Non-Chelating Aldehydes.

Kevin G M Kou1, Lauren E Longobardi2, Vy M Dong3.   

Abstract

The application of the bidentate, electron-rich bisphosphine ligand, 1,3-bis(dicyclohexyl)phosphine-propane (dcpp), in rhodium(I)-catalyzed intermolecular ketone hydroacylation is herein described. Isatins and α-keto amides are shown to undergo hydroacylation with a variety of non-chelating linear and branched aliphatic aldehydes. Also reported is the synthesis of new bidentate chiral phosphine ligands, and their application in hydroacylation is discussed.

Entities:  

Keywords:  P ligands; asymmetric catalysis; hydroacylation; ketone; rhodium

Year:  2015        PMID： 27134619      PMCID： PMC4847752          DOI： 10.1002/adsc.201500313

Source DB:  PubMed          Journal:  Adv Synth Catal        ISSN： 1615-4150            Impact factor:   5.837


  36 in total

1.  Chelation-controlled intermolecular hydroacylation: direct addition of alkyl aldehydes to functionalized alkenes.

Authors:  Michael C Willis; Steven J McNally; Paul J Beswick
Journal:  Angew Chem Int Ed Engl       Date:  2004-01-03       Impact factor: 15.336

2.  A second-generation catalyst for intermolecular hydroacylation of alkenes and alkynes using beta-S-substituted aldehydes: the role of a hemilabile P-O-P ligand.

Authors:  Gemma L Moxham; Helen E Randell-Sly; Simon K Brayshaw; Robert L Woodward; Andrew S Weller; Michael C Willis
Journal:  Angew Chem Int Ed Engl       Date:  2006-11-20       Impact factor: 15.336

3.  Rhodium-catalyzed branched-selective alkyne hydroacylation: a ligand-controlled regioselectivity switch.

Authors:  Carlos González-Rodríguez; Rebekah J Pawley; Adrian B Chaplin; Amber L Thompson; Andrew S Weller; Michael C Willis
Journal:  Angew Chem Int Ed Engl       Date:  2011-04-19       Impact factor: 15.336

4.  Catalytic hydroacylation as an approach to homoaldol products.

Authors:  Stephen K Murphy; David A Petrone; Matthew M Coulter; Vy M Dong
Journal:  Org Lett       Date:  2011-11-07       Impact factor: 6.005

5.  Scope and mechanism of the intermolecular addition of aromatic aldehydes to olefins catalyzed by Rh(I) olefin complexes.

Authors:  Amy H Roy; Christian P Lenges; Maurice Brookhart
Journal:  J Am Chem Soc       Date:  2007-01-31       Impact factor: 15.419

6.  Tunable bromomagnesium thiolate Tishchenko reaction catalysts: intermolecular aldehyde-trifluoromethylketone coupling.

Authors:  Linda Cronin; Francesco Manoni; Cornelius J O'Connor; Stephen J Connon
Journal:  Angew Chem Int Ed Engl       Date:  2010-04-12       Impact factor: 15.336

7.  Bite angle effects of diphosphines in C-C and C-X bond forming cross coupling reactions.

Authors:  Mandy-Nicole Birkholz; Zoraida Freixa; Piet W N M van Leeuwen
Journal:  Chem Soc Rev       Date:  2009-02-10       Impact factor: 54.564

8.  Double-chelation-assisted Rh-catalyzed intermolecular hydroacylation between salicylaldehydes and 1,4-penta- or 1,5-hexadienes.

Authors:  Masanori Imai; Masakazu Tanaka; Keitaro Tanaka; Yoichiro Yamamoto; Naoko Imai-Ogata; Masato Shimowatari; Shinji Nagumo; Norio Kawahara; Hiroshi Suemune
Journal:  J Org Chem       Date:  2004-02-20       Impact factor: 4.354

9.  Rhodium-catalyzed highly enantioselective direct intermolecular hydroacylation of 1,1-disubstituted alkenes with unfunctionalized aldehydes.

Authors:  Yu Shibata; Ken Tanaka
Journal:  J Am Chem Soc       Date:  2009-09-09       Impact factor: 15.419

10.  Direct intermolecular hydroacylation of N,N-dialkylacrylamides with aldehydes catalyzed by a cationic rhodium(I)/dppb complex.

Authors:  Ken Tanaka; Yu Shibata; Takeshi Suda; Yuji Hagiwara; Masao Hirano
Journal:  Org Lett       Date:  2007-03-07       Impact factor: 6.005
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  2 in total

1.  Transition-Metal-Catalyzed C-H Bond Addition to Carbonyls, Imines, and Related Polarized π Bonds.

Authors:  Joshua R Hummel; Jeffrey A Boerth; Jonathan A Ellman
Journal:  Chem Rev       Date:  2016-12-12       Impact factor: 60.622

Review 2.  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 in total

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