Literature DB >> 19789723

Synthesis of polysubstituted tetrahydrofurans via Pd-catalyzed carboetherification reactions.

Michael B Hay1, John P Wolfe.   

Abstract

Pd-catalyzed carboetherifications of 1-, 2-, or 3-substituted γ-hydroxy internal alkenes afford tetrahydrofuran products bearing three stereocenters in good yield with moderate to good stereoselectivity.

Entities:  

Year:  2006        PMID： 19789723      PMCID： PMC2752900          DOI： 10.1016/j.tetlet.2006.02.066

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  11 in total

Review 1.  Annonaceous acetogenins: recent progress.

Authors:  F Q Alali; X X Liu; J L McLaughlin
Journal:  J Nat Prod       Date:  1999-03       Impact factor: 4.050

2.  Stereochemistry of the Wacker Reaction: Modes of Addition of Hydroxide, Methoxide, and Phenyl at High and Low [Cl(-)]. A Study Using Chirality Transfer.

Authors:  Othman Hamed; Charles Thompson; Patrick M. Henry
Journal:  J Org Chem       Date:  1997-10-17       Impact factor: 4.354

3.  Strategy and methodology development for the total synthesis of polyether ionophore antibiotics.

Authors:  M M Faul; B E Huff
Journal:  Chem Rev       Date:  2000-06-14       Impact factor: 60.622

4.  Palladium-catalyzed synthesis of 2,1'-disubstituted tetrahydrofurans from gamma-hydroxy internal alkenes. Evidence for alkene insertion into a Pd-O bond and stereochemical scrambling via beta-hydride elimination.

Authors:  Michael B Hay; John P Wolfe
Journal:  J Am Chem Soc       Date:  2005-11-30       Impact factor: 15.419

5.  Oxidative cyclizations in a nonpolar solvent using molecular oxygen and studies on the stereochemistry of oxypalladation.

Authors:  Raissa M Trend; Yeeman K Ramtohul; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2005-12-21       Impact factor: 15.419

6.  Palladium-catalyzed synthesis of tetrahydrofurans from gamma-hydroxy terminal alkenes: scope, limitations, and stereoselectivity.

Authors:  Michael B Hay; Alison R Hardin; John P Wolfe
Journal:  J Org Chem       Date:  2005-04-15       Impact factor: 4.354

7.  Simplakidine A, a unique pyridinium alkaloid from the Caribbean sponge plakortis simplex.

Authors:  Claudio Campagnuolo; Caterina Fattorusso; Ernesto Fattorusso; Angela Ianaro; Barbara Pisano; Orazio Taglialatela-Scafati
Journal:  Org Lett       Date:  2003-03-06       Impact factor: 6.005

8.  Palladium-catalyzed synthesis of N-aryl pyrrolidines from gamma-(N-Arylamino) alkenes: evidence for chemoselective alkene insertion into Pd--N bonds.

Authors:  Joshua E Ney; John P Wolfe
Journal:  Angew Chem Int Ed Engl       Date:  2004-07-05       Impact factor: 15.336

9.  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.

Authors:  John P Wolfe; Michael A Rossi
Journal:  J Am Chem Soc       Date:  2004-02-18       Impact factor: 15.419

10.  Deuterium-labeling studies establishing stereochemistry at the oxypalladation step in Wacker-type oxidative cyclization of an o-allylphenol.

Authors:  Tamio Hayashi; Kaori Yamasaki; Michihiro Mimura; Yasuhiro Uozumi
Journal:  J Am Chem Soc       Date:  2004-03-17       Impact factor: 15.419
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  8 in total

1.  Highly diastereoselective Pd-catalyzed carboetherification reactions of acyclic internal alkenes. Stereoselective synthesis of polysubstituted tetrahydrofurans.

Authors:  Amanda F Ward; John P Wolfe
Journal:  Org Lett       Date:  2010-03-19       Impact factor: 6.005

2.  Recent Advances in the Stereoselective Synthesis of Tetrahydrofurans.

Authors:  John P Wolfe; Michael B Hay
Journal:  Tetrahedron       Date:  2007-01-08       Impact factor: 2.457

3.  Palladium-Catalyzed Carboetherification and Carboamination Reactions of γ-Hydroxy- and γ-Aminoalkenes for the Synthesis of Tetrahydrofurans and Pyrrolidines.

Authors:  John P Wolfe
Journal:  European J Org Chem       Date:  2007-02

4.  Synthesis of chromans via Pd-catalyzed alkene carboetherification reactions.

Authors:  Amanda F Ward; Yan Xu; John P Wolfe
Journal:  Chem Commun (Camb)       Date:  2011-11-24       Impact factor: 6.222

5.  Stereoselective Synthesis of Saturated Heterocycles via Pd-Catalyzed Alkene Carboetherification and Carboamination Reactions.

Authors:  John P Wolfe
Journal:  Synlett       Date:  2006-11-13       Impact factor: 2.454

6.  Stereoselective synthesis of isoxazolidines through Pd-catalyzed carboetherification of N-butenylhydroxylamines.

Authors:  Michael B Hay; John P Wolfe
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

7.  Synthesis of fused-ring and attached-ring bis-tetrahydrofurans via Pd-catalyzed carboetherification.

Authors:  Amanda F Ward; John P Wolfe
Journal:  Org Lett       Date:  2009-05-21       Impact factor: 6.005

8.  Palladium-catalysed cyclisation of alkenols: Synthesis of oxaheterocycles as core intermediates of natural compounds.

Authors:  Miroslav Palík; Jozef Kožíšek; Peter Koóš; Tibor Gracza
Journal:  Beilstein J Org Chem       Date:  2014-09-03       Impact factor: 2.883
  8 in total

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