Palladium-catalyzed enantioselective carboannulation of 1,3-dienes with aryl iodides enables access to chiral indanes.

Chem Commun (Camb)

Anhui Province Key Laboratory of Advanced Catalytic Materials and Reaction Engineering, School of Chemistry and Chemical Engineering, Hefei University of Technology, Hefei 230009, China.

Published: August 2018


Category Ranking

98%

Total Visits

921

Avg Visit Duration

2 minutes

Citations

20

Article Abstract

A palladium-catalyzed enantioselective carboannulation of 1,3-dienes and aryl iodides has been established by using a BINOL-based phosphoramidite ligand. This reaction proceeded via a tandem Heck-type insertion and asymmetric intramolecular Tsuji-Trost allylic alkylation, providing indane derivatives with high levels of enantioselectivity (up to >99% ee).

Download full-text PDF

Source
http://dx.doi.org/10.1039/c8cc04641gDOI Listing

Publication Analysis

Top Keywords

palladium-catalyzed enantioselective
8
enantioselective carboannulation
8
carboannulation 13-dienes
8
13-dienes aryl
8
aryl iodides
8
iodides enables
4
enables access
4
access chiral
4
chiral indanes
4
indanes palladium-catalyzed
4

Similar Publications

Palladium-Catalyzed Asymmetric Aminomethylative Pyridonation of Conjugated Dienes.

Org Lett

September 2025

State Key Laboratory of Precision and Intelligent Chemistry, Department of Chemistry, University of Science and Technology of China, Hefei 230026, P. R. China.

A novel palladium-catalyzed asymmetric aminomethylative pyridonation of conjugated dienes with -acetals and 2-hydroxypyridines was established, which provided a direct and reliable method for the synthesis of a wide range of γ-aminated N-substituted 2-pyridones with good to excellent enantioselectivities. The simple BF was identified as an effective cocatalyst to improve the reaction efficiency, and DFT calculations revealed that proton transfer between the aminomethylated allylic palladium species and 2-hydroxypyridine promoted by BF is crucial for obtaining good reactivity.

View Article and Find Full Text PDF

A series of axially chiral 5,5'-substituted 2,2'-bipyridine ligands featuring tunable properties have been synthesized. These ligands have been successfully applied to palladium-catalyzed asymmetric oxidative [2 + 2] annulation of arylboronic acids and alkenes, providing a diverse range of chiral benzocyclobutenes in excellent enantioselectivities with a broad substrate scope.

View Article and Find Full Text PDF

Noncovalent Interactions in the Palladium-Catalyzed Diastereo- and Enantioselective Hydroalkylation of Alkoxyallenes with 2-Acylimidazoles.

Org Lett

August 2025

State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, Engineering Research Center of Photoresist Materials, Ministry of Education, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, Jiangsu 210023, China.

A palladium-catalyzed diastereo- and enantioselective hydroalkylation of alkoxyallenes with 2-acylimidazoles has been developed featuring ()-DTBM-Garphos as a chiral ligand and 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) as an additive, providing access to enantiomerically pure carbonyl compounds bearing two vicinal acyclic stereogenic carbon centers with excellent stereocontrol (up to 20:1 dr and 97% ee).

View Article and Find Full Text PDF

Herein, we report a palladium-catalyzed atroposelective C-H vinylation approach for the construction of axially chiral biaryls featuring vinyl substituents, enabled by a chiral transient directing group. Notably, this transformation proceeds efficiently with vinyl silane as the vinyl source, without requiring any external fluoride additives. This protocol exhibits a broad substrate scope, efficiently transforming diverse biaryl-2-aldehydes into atroposelective vinylated products in excellent yields with high enantioselectivities up to >99.

View Article and Find Full Text PDF

Palladium-Catalyzed Enantioselective Aryl-thiolation of Indoles: An Approach to Chiral Thioindoline.

Org Lett

August 2025

School of Pharmacy and Science, Key Laboratory of Anti-inflammatory and Immune Medicine, Ministry of Education, Institute of Clinical Pharmacology, Anhui Medical University, Hefei, Anhui 230032, China.

We developed a palladium-catalyzed enantioselectivity dearomative thio-arylation reaction of indoles. The reaction constructs thioindolines by a single operation. The reaction has excellent diastereoselectivities (>20:1 dr) and enantioselectivities (78-91% ee), a broad substrate scope, as well as a good tolerance of functional groups.

View Article and Find Full Text PDF