Unknown

Dataset Information

0

Catalytic Asymmetric Synthesis of Branched Chiral Allylic Phenyl Ethers from (E)-Allylic Alcohols.

ABSTRACT: The first di-?-amidate dipalladium complexes and a new di-?-carboxylate dipalladium complex of the COP (cobalt oxazoline palladacycle) palladium(II) catalyst family are reported and characterized crystallographically. The di-?-amidate complex 3 or its enantiomer (ent-3) are the first asymmetric catalysts that allow commercially available, or readily accessible, (E)-2-alkene-1-ols to be transformed to enantioenriched branched allylic aryl ethers upon reaction of their trichloroacetimidate derivatives with phenols. The 3-aryloxy-1-alkene products are formed in high enantiomeric purity (typically 90-98% ee) and useful yields (61-88%).

SUBMITTER: Olson AC 

PROVIDER: S-EPMC3689305 | biostudies-literature | 2009 Dec

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

Catalytic Asymmetric Synthesis of Branched Chiral Allylic Phenyl Ethers from (<i>E</i>)-Allylic Alcohols.

Olson Angela C AC   Overman Larry E LE   Sneddon Helen F HF   Ziller Joseph W JW  

Advanced synthesis & catalysis 20091201 18

The first di-μ-amidate dipalladium complexes and a new di-μ-carboxylate dipalladium complex of the COP (cobalt oxazoline palladacycle) palladium(II) catalyst family are reported and characterized crystallographically. The di-μ-amidate complex <b>3</b> or its enantiomer (<i>ent</i>-<b>3</b>) are the first asymmetric catalysts that allow commercially available, or readily accessible, (<i>E</i>)-2-alkene-1-ols to be transformed to enantioenriched branched allylic aryl ethers upon reaction of their  ...[more]

Similar Datasets

Unknown Catalytic asymmetric synthesis of chiral allylic esters.
| S-EPMC2966826 | biostudies-other
Unknown Catalytic asymmetric generation of (Z)-disubstituted allylic alcohols.
| S-EPMC2532596 | biostudies-literature
Unknown New Nitrogen, Sulfur-, and Selenium-Donating Ligands Derived from Chiral Pyridine Amino Alcohols. Synthesis and Catalytic Activity in Asymmetric Allylic Alkylation.
| S-EPMC8228606 | biostudies-literature
Unknown Solid-phase synthesis of chiral 3,4-diazaphospholanes and their application to catalytic asymmetric allylic alkylation.
| S-EPMC397399 | biostudies-other
Unknown Catalytic asymmetric synthesis of allylic thiol derivatives.
| S-EPMC3064473 | biostudies-other
Unknown Pd-catalyzed synthesis of allylic silanes from allylic ethers.
| S-EPMC2804976 | biostudies-literature
Unknown Stereoselective synthesis of cyclic ethers via the palladium-catalyzed intramolecular addition of alcohols to phosphono allylic carbonates.
| S-EPMC2717013 | biostudies-literature
Unknown Direct catalytic asymmetric synthesis of α-chiral bicyclo[1.1.1]pentanes.
| S-EPMC7955048 | biostudies-literature
Unknown Catalytic Regio- and Enantioselective Haloazidation of Allylic Alcohols.
| S-EPMC6499076 | biostudies-literature
Unknown Development of Zn-ProPhenol-catalyzed asymmetric alkyne addition: synthesis of chiral propargylic alcohols.
| S-EPMC3864595 | biostudies-literature