Literature DB >> 28128936

Rhodium-Catalyzed Hydrofunctionalization: Enantioselective Coupling of Indolines and 1,3-Dienes.

Xiao-Hui Yang1, Vy M Dong1.   

Abstract

We communicate a strategy for the hydrofunctionalization of 1,3-dienes via Rh-hydride catalysis. Conjugated dienes are coupled to nucleophiles to demonstrate the feasibility of novel C-C, C-O, C-S, and C-N bond forming processes. In the presence of a chiral JoSPOphos ligand, hydroamination generates chiral allylic amines with high regio- and enantioselectivity. Tuning both the pKa and steric properties of an acid-additive is critical for enantiocontrol.

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Year:  2017        PMID： 28128936      PMCID： PMC6857534          DOI： 10.1021/jacs.6b12307

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


  53 in total

1.  Palladium-catalyzed hydroamination of 1,3-dienes: a colorimetric assay and enantioselective additions.

Authors:  O Löber; M Kawatsura; J F Hartwig
Journal:  J Am Chem Soc       Date:  2001-05-09       Impact factor: 15.419

2.  A general catalytic hydroamidation of 1,3-dienes: atom-efficient synthesis of N-allyl heterocycles, amides, and sulfonamides.

Authors:  Debasis Banerjee; Kathrin Junge; Matthias Beller
Journal:  Angew Chem Int Ed Engl       Date:  2014-01-22       Impact factor: 15.336

3.  A palladium-catalyzed three-component cross-coupling of conjugated dienes or terminal alkenes with vinyl triflates and boronic acids.

Authors:  Longyan Liao; Ranjan Jana; Kaveri Balan Urkalan; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2011-03-30       Impact factor: 15.419

4.  Ruthenium catalyzed hydrohydroxyalkylation of isoprene with heteroaromatic secondary alcohols: isolation and reversible formation of the putative metallacycle intermediate.

Authors:  Boyoung Y Park; T Patrick Montgomery; Victoria J Garza; Michael J Krische
Journal:  J Am Chem Soc       Date:  2013-10-24       Impact factor: 15.419

5.  Asymmetric hydrovinylation of 1-vinylcycloalkenes. Reagent control of regio- and stereoselectivity.

Authors:  Jordan P Page; T V RajanBabu
Journal:  J Am Chem Soc       Date:  2012-03-30       Impact factor: 15.419

6.  Enantioselective Formation of All-Carbon Quaternary Centers via C-H Functionalization of Methanol: Iridium-Catalyzed Diene Hydrohydroxymethylation.

Authors:  Khoa D Nguyen; Daniel Herkommer; Michael J Krische
Journal:  J Am Chem Soc       Date:  2016-10-20       Impact factor: 15.419

7.  Asymmetric hydrovinylation of unactivated linear 1,3-dienes.

Authors:  Rakesh K Sharma; T V RajanBabu
Journal:  J Am Chem Soc       Date:  2010-03-17       Impact factor: 15.419

8.  Branching Out: Rhodium-Catalyzed Allylation with Alkynes and Allenes.

Authors:  Philipp Koschker; Bernhard Breit
Journal:  Acc Chem Res       Date:  2016-07-25       Impact factor: 22.384

9.  Gold(I)-catalyzed enantioselective hydroamination of N-allenyl carbamates.

Authors:  Zhibin Zhang; Christopher F Bender; Ross A Widenhoefer
Journal:  Org Lett       Date:  2007-06-27       Impact factor: 6.005

Review 10.  Synthetic Strategies toward Natural Products Containing Contiguous Stereogenic Quaternary Carbon Atoms.

Authors:  Martin Büschleb; Stéphane Dorich; Stephen Hanessian; Daniel Tao; Kyle B Schenthal; Larry E Overman
Journal:  Angew Chem Int Ed Engl       Date:  2016-02-02       Impact factor: 15.336
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  22 in total

1.  Catalytic Hydrothiolation: Regio- and Enantioselective Coupling of Thiols and Dienes.

Authors:  Xiao-Hui Yang; Ryan T Davison; Vy M Dong
Journal:  J Am Chem Soc       Date:  2018-08-09       Impact factor: 15.419

2.  Multimetallic Ni- and Pd-Catalyzed Cross-Electrophile Coupling To Form Highly Substituted 1,3-Dienes.

Authors:  Astrid M Olivares; Daniel J Weix
Journal:  J Am Chem Soc       Date:  2018-02-08       Impact factor: 15.419

3.  Catalytic Hydrothiolation: Counterion-Controlled Regioselectivity.

Authors:  Xiao-Hui Yang; Ryan T Davison; Shao-Zhen Nie; Faben A Cruz; Tristan M McGinnis; Vy M Dong
Journal:  J Am Chem Soc       Date:  2019-02-08       Impact factor: 15.419

4.  Site-Selective Nitrene Transfer to Conjugated Olefins Directed by Oxazoline Peptide Ligands.

Authors:  Golo Storch; Naudin van den Heuvel; Scott J Miller
Journal:  Adv Synth Catal       Date:  2020-01-23       Impact factor: 5.837

5.  Preparation of Chiral Allenes through Pd-Catalyzed Intermolecular Hydroamination of Conjugated Enynes: Enantioselective Synthesis Enabled by Catalyst Design.

Authors:  Nathan J Adamson; Haleh Jeddi; Steven J Malcolmson
Journal:  J Am Chem Soc       Date:  2019-05-15       Impact factor: 15.419

6.  Pyridine(diimine) Iron Diene Complexes Relevant to Catalytic [2+2]-Cycloaddition Reactions.

Authors:  C Rose Kennedy; Hongyu Zhong; Matthew V Joannou; Paul J Chirik
Journal:  Adv Synth Catal       Date:  2019-11-19       Impact factor: 5.837

Review 7.  Alkynes as Electrophilic or Nucleophilic Allylmetal Precursors in Transition-Metal Catalysis.

Authors:  Alexander M Haydl; Bernhard Breit; Tao Liang; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2017-08-10       Impact factor: 15.336

8.  Enantioselective Coupling of Dienes and Phosphine Oxides.

Authors:  Shao-Zhen Nie; Ryan T Davison; Vy M Dong
Journal:  J Am Chem Soc       Date:  2018-11-19       Impact factor: 15.419

9.  A Diverted Aerobic Heck Reaction Enables Selective 1,3-Diene and 1,3,5-Triene Synthesis through C-C Bond Scission.

Authors:  Neil J McAlpine; Long Wang; Brad P Carrow
Journal:  J Am Chem Soc       Date:  2018-10-15       Impact factor: 15.419

10.  Highly Stereoselective and Catalytic Desulfitative C-O and C-I Dienylation with Sulfolenes: the Importance of Basic Additives.

Authors:  Hang T Dang; Viet D Nguyen; Hoang H Pham; Hadi D Arman; Oleg V Larionov
Journal:  Tetrahedron       Date:  2019-04-08       Impact factor: 2.457
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