Unknown

Dataset Information

0

Enantioselective ?-Benzylation of Acyclic Esters Using ?-Extended Electrophiles.

ABSTRACT: The first asymmetric cooperative Lewis base/palladium catalyzed benzylic alkylation of acyclic esters is reported. This reaction proceeds via stereodefined C1-ammonium enolate nucleophiles. Critical to its success was the identification of benzylic phosphate electrophiles, which were uniquely reactive. Alkylated products were obtained with very high levels of enantioselectivity, and this method has been applied toward the synthesis of the thrombin inhibitor DX-9065a.

SUBMITTER: Schwarz KJ 

PROVIDER: S-EPMC6499373 | biostudies-literature | 2018 Sep

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

Enantioselective α-Benzylation of Acyclic Esters Using π-Extended Electrophiles.

Schwarz Kevin J KJ   Yang Chao C   Fyfe James W B JWB   Snaddon Thomas N TN  

Angewandte Chemie (International ed. in English) 20180820 37

The first asymmetric cooperative Lewis base/palladium catalyzed benzylic alkylation of acyclic esters is reported. This reaction proceeds via stereodefined C1-ammonium enolate nucleophiles. Critical to its success was the identification of benzylic phosphate electrophiles, which were uniquely reactive. Alkylated products were obtained with very high levels of enantioselectivity, and this method has been applied toward the synthesis of the thrombin inhibitor DX-9065a. ...[more]

Similar Datasets

Unknown Enantioselective α-Allylation of Acyclic Esters Using B(pin)-Substituted Electrophiles: Independent Regulation of Stereocontrol Elements through Cooperative Pd/Lewis Base Catalysis.
| S-EPMC6515920 | biostudies-literature
Unknown Enantioselective Benzylation and Allylation of α-Trifluoromethoxy Indanones under Phase-Transfer Catalysis.
| S-EPMC6696116 | biostudies-literature
Unknown Traversing Steric Limitations by Cooperative Lewis Base/Palladium Catalysis: An Enantioselective Synthesis of ?-Branched Esters Using 2-Substituted Allyl Electrophiles.
| S-EPMC6038818 | biostudies-literature
Unknown Enantioselective ?-benzylation of aldehydes via photoredox organocatalysis.
| S-EPMC3056320 | biostudies-literature
Unknown Light-Driven Enantioselective Organocatalytic ?-Benzylation of Enals.
| S-EPMC5412672 | biostudies-literature
Unknown Enantioselective <i>α</i>-Allylation of Aryl Acetic Acid Esters via C1-Ammonium Enolate Nucleophiles: Identification of a Broadly Effective Palladium Catalyst for Electron-Deficient Electrophiles.
| S-EPMC6519469 | biostudies-literature
Unknown Photocatalytic enantioselective α-aminoalkylation of acyclic imine derivatives by a chiral copper catalyst.
| S-EPMC6707287 | biostudies-other
Unknown Palladium-Catalyzed Allylation/Benzylation of H-Phosphinate Esters with Alcohols.
| S-EPMC6273960 | biostudies-literature
Unknown Palladium-Catalyzed Enantioselective Decarboxylative Allylic Alkylation of Acyclic α-<i>N</i>-Pyrrolyl/Indolyl Ketones.
| S-EPMC7608871 | biostudies-literature
Unknown Enantioselective Heck arylations of acyclic alkenyl alcohols using a redox-relay strategy.
| S-EPMC3583361 | biostudies-literature