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Literature DB >> 28267330

Study of Intermediates in Iridium-(Phosphoramidite,Olefin)-Catalyzed Enantioselective Allylic Substitution.

Simon L Rössler¹, Simon Krautwald¹, Erick M Carreira¹.

Abstract

Experimental mechanistic studies of iridium-catalyzed, enantioselective allylic substitution enabled by (phosphoramidite,olefin) ligands are reported. (η2-Allylic alcohol)iridium(I) and (η3-allyl)iridium(III) complexes were synthesized and characterized by NMR spectroscopy as well as X-ray crystallography. The substrate complexes are catalytically and kinetically competent to be intermediates in allylic substitutions of branched, racemic allylic alcohols with various nucleophiles. In addition, we have identified an off-cycle pathway involving reversible binding of molecular oxygen to iridium, which contributes to the air tolerance of the catalyst system.

Entities: Chemical Gene

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Year: 2017 PMID： 28267330 DOI： 10.1021/jacs.6b12421

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

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Cited

9 in total

1. Regio- and Enantioselective Iridium-Catalyzed N-Allylation of Indoles and Related Azoles with Racemic Branched Alkyl-Substituted Allylic Acetates.

Authors: Seung Wook Kim; Tabitha T Schempp; Jason R Zbieg; Craig E Stivala; Michael J Krische
Journal: Angew Chem Int Ed Engl Date: 2019-05-06 Impact factor: 15.336

2. Regio- and Enantioselective Iridium-Catalyzed Amination of Racemic Branched Alkyl-Substituted Allylic Acetates with Primary and Secondary Aromatic and Heteroaromatic Amines.

Authors: Seung Wook Kim; Leyah A Schwartz; Jason R Zbieg; Craig E Stivala; Michael J Krische
Journal: J Am Chem Soc Date: 2018-12-20 Impact factor: 15.419

3. Amphiphilic π-Allyliridium C,O-Benzoates Enable Regio- and Enantioselective Amination of Branched Allylic Acetates Bearing Linear Alkyl Groups.

Authors: Arismel Tena Meza; Thomas Wurm; Lewis Smith; Seung Wook Kim; Jason R Zbieg; Craig E Stivala; Michael J Krische
Journal: J Am Chem Soc Date: 2018-01-19 Impact factor: 15.419

4. Enantioselective and Diastereodivergent Allylation of Propargylic C-H Bonds.

Authors: Jin Zhu; Yidong Wang; Aaron D Charlack; Yi-Ming Wang
Journal: J Am Chem Soc Date: 2022-08-17 Impact factor: 16.383

5. Enantioselective Synthesis of Acyclic α-Quaternary Carboxylic Acid Derivatives through Iridium-Catalyzed Allylic Alkylation.

Authors: Samantha E Shockley; J Caleb Hethcox; Brian M Stoltz
Journal: Angew Chem Int Ed Engl Date: 2017-08-09 Impact factor: 15.336

Study of Intermediates in Iridium-(Phosphoramidite,Olefin)-Catalyzed Enantioselective Allylic Substitution.

1. Regio- and Enantioselective Iridium-Catalyzed N-Allylation of Indoles and Related Azoles with Racemic Branched Alkyl-Substituted Allylic Acetates.

2. Regio- and Enantioselective Iridium-Catalyzed Amination of Racemic Branched Alkyl-Substituted Allylic Acetates with Primary and Secondary Aromatic and Heteroaromatic Amines.

3. Amphiphilic π-Allyliridium C,O-Benzoates Enable Regio- and Enantioselective Amination of Branched Allylic Acetates Bearing Linear Alkyl Groups.

4. Enantioselective and Diastereodivergent Allylation of Propargylic C-H Bonds.

5. Enantioselective Synthesis of Acyclic α-Quaternary Carboxylic Acid Derivatives through Iridium-Catalyzed Allylic Alkylation.

6. Intermolecular Stereoselective Iridium-Catalyzed Allylic Alkylation: An Evolutionary Account.

7. Enantioselective Allylation of Alkenyl Boronates Promotes a 1,2-Metalate Rearrangement with 1,3-Diastereocontrol.

8. Enantio- and Diastereoselective Suzuki-Miyaura Coupling with Racemic Bicycles.

9. Iridium-Catalyzed Enantioselective Intermolecular Indole C2-Allylation.