Literature DB >> 26366747

Development of Enantioselective Palladium-Catalyzed Alkene Carboalkoxylation Reactions for the Synthesis of Tetrahydrofurans.

Brett A Hopkins1, Zachary J Garlets1, John P Wolfe2.   

Abstract

The Pd-catalyzed coupling of γ-hydroxyalkenes with aryl bromides affords enantiomerically enriched 2-(arylmethyl)tetrahydrofuran derivatives in good yield and up to 96:4 e.r. This transformation was achieved through the development of a new TADDOL/2-arylcyclohexanol-derived chiral phosphite ligand. The transformations are effective with an array of different aryl bromides, and can be used for the preparation of products bearing quaternary stereocenters.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  asymmetric catalysis; enantioselective synthesis; heterocycles; palladium

Mesh：

Substances：

Year:  2015        PMID： 26366747      PMCID： PMC4711365          DOI： 10.1002/anie.201506884

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


  19 in total

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7.  Asymmetric palladium-catalyzed carboamination reactions for the synthesis of enantiomerically enriched 2-(arylmethyl)- and 2-(alkenylmethyl)pyrrolidines.

Authors:  Duy N Mai; John P Wolfe
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8.  Stereoselective synthesis of tetrahydrofurans via the palladium-catalyzed reaction of aryl bromides with gamma-hydroxy alkenes: evidence for an unusual intramolecular olefin insertion into a Pd(Ar)(OR) intermediate.

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5.  Synthesis of Phthalans Via Copper-Catalyzed Enantioselective Cyclization/Carboetherification of 2-Vinylbenzyl Alcohols.

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6.  Catalytic enantioselective oxidative coupling of saturated ethers with carboxylic acid derivatives.

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7.  Effects of ligands on the migratory insertion of alkenes into rhodium-oxygen bonds.

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