Literature DB >> 18351772

Efficient, selective, and green: catalyst tuning for highly enantioselective reactions of ethylene.

Craig R Smith1, T V RajanBabu.   

Abstract

Fine tuning of the biaryl and amino moieties of Feringa's phosphoramidite ligands yields structurally simpler, yet more efficient and selective, ligands for asymmetric hydrovinylation of vinylarenes and acylic 1,3-dienes. The enantioselectivities and yields observed in the formation of the 3-arylbutenes are among the highest for all asymmetric catalytic processes reported to date for the synthesis of intermediates for the widely used antiinflammatory 2-arylpropionic acids including naproxen, ibuprofen, fenoprofen, and flurbiprofen.

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Year:  2008        PMID: 18351772      PMCID: PMC2746057          DOI: 10.1021/ol800395m

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  18 in total

1.  Asymmetric hydrovinylation reaction.

Authors:  T V RajanBabu
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

2.  Hydrovinylation of 1,3-dienes: a new protocol, an asymmetric variation, and a potential solution to the exocyclic side chain stereochemistry problem.

Authors:  Aibin Zhang; T V RajanBabu
Journal:  J Am Chem Soc       Date:  2006-01-11       Impact factor: 15.419

3.  Highly enantioselective hydrovinylation of alpha-alkyl vinylarenes. an approach to the construction of all-carbon quaternary stereocenters.

Authors:  Wen-Jian Shi; Qi Zhang; Jian-Hua Xie; Shou-Fei Zhu; Guo-Hua Hou; Qi-Lin Zhou
Journal:  J Am Chem Soc       Date:  2006-03-08       Impact factor: 15.419

4.  Enantioselective rhodium-catalyzed [2+2+2] cycloaddition of alkenyl isocyanates and terminal alkynes: application to the total synthesis of (+)-lasubine II.

Authors:  Robert T Yu; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2006-09-27       Impact factor: 15.419

5.  Nickel(0)-catalyzed asymmetric hydrocyanation of 1,3-dienes.

Authors:  Biswajit Saha; T V Rajanbabu
Journal:  Org Lett       Date:  2006-09-28       Impact factor: 6.005

Review 6.  Phosphoramidites: marvellous ligands in catalytic asymmetric conjugate addition.

Authors:  B L Feringa
Journal:  Acc Chem Res       Date:  2000-06       Impact factor: 22.384

7.  PipPhos and MorfPhos: privileged monodentate phosphoramidite ligands for rhodium-catalyzed asymmetric hydrogenation.

Authors:  Heiko Bernsmann; Michel van den Berg; Rob Hoen; Adriaan J Minnaard; Gerlinde Mehler; Manfred T Reetz; Johannes G De Vries; Ben L Feringa
Journal:  J Org Chem       Date:  2005-02-04       Impact factor: 4.354

8.  Regio- and stereoselective ruthenium-catalyzed hydrovinylation of 1,3-dienes: application to the generation of a 20(S) steroidal side chain.

Authors:  Zhengjie He; Chae S Yi; William A Donaldson
Journal:  Org Lett       Date:  2003-05-01       Impact factor: 6.005

9.  Fine-tuning monophosphine ligands for enhanced enantioselectivity. Influence of chiral hemilabile pendant groups.

Authors:  Aibin Zhang; T V RajanBabu
Journal:  Org Lett       Date:  2004-04-29       Impact factor: 6.005

10.  Hydrovinylation of norbornene. Ligand-dependent selectivity and asymmetric variations.

Authors:  Ramaiah Kumareswaran; Malay Nandi; T V RajanBabu
Journal:  Org Lett       Date:  2003-11-13       Impact factor: 6.005

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  20 in total

1.  Triarylphosphine Ligands with Hemilabile Alkoxy Groups. Ligands for Nickel(II)-Catalyzed Olefin Dimerization Reactions. Hydrovinylation of Vi-nylarenes, 1,3-Dienes, and Cycloisomerization of 1,6-Dienes.

Authors:  Souvagya Biswas; Aibin Zhang; Balaram Raya; T V RajanBabu
Journal:  Adv Synth Catal       Date:  2014-07-01       Impact factor: 5.837

2.  (R)-2,2'-BINAPHTHOYL-(S,S)-DI(1-PHENYLETHYL) AMINOPHOSPHINE. SCALABLE PROTOCOLS FOR THE SYNTHESES OF PHOSPHORAMIDITE (FERINGA) LIGANDS.

Authors:  Craig R Smith; Daniel J Mans; T V Rajanbabu; Scott E Denmark; Son T Nguyen
Journal:  Organic Synth       Date:  2008

3.  (R)-3-METHYL-3-PHENYL-1-PENTENE VIA CATALYTIC ASYMMETRIC HYDROVINYLATION.

Authors:  Craig R Smith; Aibin Zhang; Daniel J Mans; T V Rajanbabu; Scott E Denmark; Min Xie
Journal:  Organic Synth       Date:  2008

4.  Low Pressure Vinylation of Aryl and Vinyl Halides via Heck-Mizoroki Reactions Using Ethylene.

Authors:  Craig R Smith; T V Rajanbabu
Journal:  Tetrahedron       Date:  2010-01-30       Impact factor: 2.457

5.  Acyclic Quaternary Carbon Stereocenters via Enantioselective Transition Metal Catalysis.

Authors:  Jiajie Feng; Michael Holmes; Michael J Krische
Journal:  Chem Rev       Date:  2017-09-14       Impact factor: 60.622

6.  Ethylene in organic synthesis. Repetitive hydrovinylation of alkenes for highly enantioselective syntheses of pseudopterosins.

Authors:  Daniel J Mans; G Adam Cox; T V RajanBabu
Journal:  J Am Chem Soc       Date:  2011-03-30       Impact factor: 15.419

7.  Asymmetric hydrovinylation of vinylindoles. A facile route to cyclopenta[g]indole natural products (+)-cis-trikentrin A and (+)-cis-trikentrin B.

Authors:  Wang Liu; Hwan Jung Lim; T V RajanBabu
Journal:  J Am Chem Soc       Date:  2012-03-13       Impact factor: 15.419

8.  In Pursuit of an Ideal C-C Bond-Forming Reaction: Development and Applications of the Hydrovinylation of Olefins.

Authors:  T V Rajanbabu
Journal:  Synlett       Date:  2009       Impact factor: 2.454

9.  Facile Pd(II)- and Ni(II)-catalyzed isomerization of terminal alkenes into 2-alkenes.

Authors:  Hwan Jung Lim; Craig R Smith; T V RajanBabu
Journal:  J Org Chem       Date:  2009-06-19       Impact factor: 4.354

10.  Tunable Phosphoramidite Ligands for Asymmetric Hydrovinylation: Ligands par excellence for Generation of All-Carbon Quaternary Centers.

Authors:  Craig R Smith; Hwan Jung Lim; Aibin Zhang; T V Rajanbabu
Journal:  Synthesis (Stuttg)       Date:  2009-01-01       Impact factor: 3.157

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