Literature DB >> 20687551

Synthesis of quaternary carbon centers via hydroformylation.

X Sun1, K Frimpong, K L Tan.   

Abstract

The application of hydroformylation to the synthesis of quaternary carbon centers is reported. The synthesis of the highly substituted carbon is achieved by applying a catalytic amount of 1. Ligand 1 serves as a catalytic directing group by covalently and reversibly binding to both the substrate and catalyst. The intramolecular nature of the directing group strategy accelerates the hydroformylation reaction such that the reaction is performed at mild temperatures (35-55 degrees C) and with excellent regioselectivity (b:l > 94:6).

Entities:  

Mesh:

Substances:

Year:  2010        PMID: 20687551      PMCID: PMC2928406          DOI: 10.1021/ja1036226

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  13 in total

1.  Highly regioselective and diastereoselective directed hydroformylation of allylic ethers: a new approach to propionate aldol synthesis.

Authors:  I J Krauss; C C Wang; J L Leighton
Journal:  J Am Chem Soc       Date:  2001-11-21       Impact factor: 15.419

2.  Synthetic aspects of stereoselective hydroformylation.

Authors:  Bernhard Breit
Journal:  Acc Chem Res       Date:  2003-04       Impact factor: 22.384

3.  Sequential enolboration/hydroformylation/aldol addition: a new one-pot cascade reaction for the regio- and diastereoselective formation of carbocyclic quaternary centres from acyclic olefins.

Authors:  Mark D Keränen; Peter Eilbracht
Journal:  Org Biomol Chem       Date:  2004-05-25       Impact factor: 3.876

4.  Regioselective hydroformylation of sulfonamides using a scaffolding ligand.

Authors:  Amanda D Worthy; Moriah M Gagnon; Michael T Dombrowski; Kian L Tan
Journal:  Org Lett       Date:  2009-07-02       Impact factor: 6.005

5.  Branched-regioselective hydroformylation with catalytic amounts of a reversibly bound directing group.

Authors:  Christian U Grünanger; Bernhard Breit
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

6.  Rhodium-catalyzed hydroformylation of cyclopropenes.

Authors:  William M Sherrill; Michael Rubin
Journal:  J Am Chem Soc       Date:  2008-09-20       Impact factor: 15.419

7.  Catalytic scaffolding ligands: an efficient strategy for directing reactions.

Authors:  Thomas E Lightburn; Michael T Dombrowski; Kian L Tan
Journal:  J Am Chem Soc       Date:  2008-06-25       Impact factor: 15.419

8.  Remote control of regio- and diastereoselectivity in the hydroformylation of bishomoallylic alcohols with catalytic amounts of a reversibly bound directing group.

Authors:  Christian U Grünanger; Bernhard Breit
Journal:  Angew Chem Int Ed Engl       Date:  2010       Impact factor: 15.336

9.  Highly regioselective rhodium-catalysed hydroformylation of unsaturated esters: the first practical method for quaternary selective carbonylation.

Authors:  Matthew L Clarke; Geoffrey J Roff
Journal:  Chemistry       Date:  2006-10-25       Impact factor: 5.236

10.  Hydroformylation reaction of alkylidenecyclopropane derivatives: a new pathway for the formation of acyclic aldehydes containing quaternary stereogenic carbons.

Authors:  Samah Simaan; Ilan Marek
Journal:  J Am Chem Soc       Date:  2010-03-31       Impact factor: 15.419

View more
  7 in total

1.  Scaffolding catalysts: highly enantioselective desymmetrization reactions.

Authors:  Xixi Sun; Amanda D Worthy; Kian L Tan
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-07       Impact factor: 15.336

2.  Scaffolding Catalysis: Expanding the Repertoire of Bifunctional Catalysts.

Authors:  Kian L Tan; Xixi Sun; Amanda D Worthy
Journal:  Synlett       Date:  2012-02-01       Impact factor: 2.454

3.  Application of a chiral scaffolding ligand in catalytic enantioselective hydroformylation.

Authors:  Amanda D Worthy; Candice L Joe; Thomas E Lightburn; Kian L Tan
Journal:  J Am Chem Soc       Date:  2010-10-27       Impact factor: 15.419

4.  Enantioselective hydroformylation of aniline derivatives.

Authors:  Candice L Joe; Kian L Tan
Journal:  J Org Chem       Date:  2011-08-15       Impact factor: 4.354

5.  Regioselective hydroformylation of allylic alcohols.

Authors:  Thomas E Lightburn; Omar A De Paolis; Ka H Cheng; Kian L Tan
Journal:  Org Lett       Date:  2011-04-19       Impact factor: 6.005

6.  Distal-selective hydroformylation using scaffolding catalysis.

Authors:  Candice L Joe; Thomas P Blaisdell; Allison F Geoghan; Kian L Tan
Journal:  J Am Chem Soc       Date:  2014-06-06       Impact factor: 15.419

Review 7.  Supramolecular Approaches To Control Activity and Selectivity in Hydroformylation Catalysis.

Authors:  Sandra S Nurttila; Pim R Linnebank; Tetiana Krachko; Joost N H Reek
Journal:  ACS Catal       Date:  2018-03-09       Impact factor: 13.084

  7 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.