Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 Palladium-Catalyzed Construction of Quaternary Stereocenters by Enantioselective Arylation of γ-Lactams with Aryl Chlorides and Bromides.

Literature DB >> 30677201

Palladium-Catalyzed Construction of Quaternary Stereocenters by Enantioselective Arylation of γ-Lactams with Aryl Chlorides and Bromides.

Carina I Jette¹, Irina Geibel¹, Shoshana Bachman¹, Masaki Hayashi¹, Shunya Sakurai¹, Hideki Shimizu¹, Jeremy B Morgan², Brian M Stoltz¹.

Abstract

Herein, we report the first Pd-catalyzed enantioselective arylation of α-substituted γ-lactams. Two sets of conditions were developed for this transformation, allowing for the use of either aryl chlorides or bromides as electrophiles. Utilizing a highly electron-rich dialkylphosphine ligand we have been able to construct α-quaternary centers in good yields (up to 91 % yield) and high enantioselectivities (up to 97 % ee).

Entities: Chemical

Keywords: asymmetric catalysis; nitrogen heterocycles; palladium; quaternary stereocenters; α-arylation

Year: 2019 PMID： 30677201 DOI： 10.1002/anie.201814475

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

Keyword Cloud
Cited

6 in total

1. Enantioselective Michael-Proton Transfer-Lactamization for Pyroglutamic Acid Derivatives: Synthesis of Dimethyl-(S,E)-5-oxo-3-styryl-1-tosylpyrrolidine-2,2-dicarboxylate.

Authors: Christian M Chaheine; Conner J Song; Paul T Gladen; Daniel Romo
Journal: Organic Synth Date: 2021

2. Enantioconvergent Alkylations of Amines by Alkyl Electrophiles: Copper-Catalyzed Nucleophilic Substitutions of Racemic α-Halolactams by Indoles.

Authors: Agnieszka Bartoszewicz; Carson D Matier; Gregory C Fu
Journal: J Am Chem Soc Date: 2019-09-09 Impact factor: 15.419

3. A Facile Direct Route to N-(Un)substituted Lactams by Cycloamination of Oxocarboxylic Acids without External Hydrogen.

Authors: Hu Li; Hongguo Wu; Heng Zhang; Yaqiong Su; Song Yang; Emiel J M Hensen
Journal: ChemSusChem Date: 2019-07-17 Impact factor: 8.928

Palladium-Catalyzed Construction of Quaternary Stereocenters by Enantioselective Arylation of γ-Lactams with Aryl Chlorides and Bromides.

1. Enantioselective Michael-Proton Transfer-Lactamization for Pyroglutamic Acid Derivatives: Synthesis of Dimethyl-(S,E)-5-oxo-3-styryl-1-tosylpyrrolidine-2,2-dicarboxylate.

2. Enantioconvergent Alkylations of Amines by Alkyl Electrophiles: Copper-Catalyzed Nucleophilic Substitutions of Racemic α-Halolactams by Indoles.

3. A Facile Direct Route to N-(Un)substituted Lactams by Cycloamination of Oxocarboxylic Acids without External Hydrogen.

4. Enantioselective Hydrocarbamoylation of Alkenes.

5. Ni-catalyzed carbamoylation of unactivated alkenes for stereoselective construction of six-membered lactams.

6. Computational Analysis of Enantioselective Pd-Catalyzed α-Arylation of Ketones.