Literature DB >> 14871078

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.

John P Wolfe1, Michael A Rossi.   

Abstract

A new, stereoselective method for the synthesis of substituted tetrahydrofurans from gamma-hydroxy alkenes that forms both a C-C and a C-O bond with diastereoselectivities of up to >20:1 is described. Initial mechanistic studies that suggest the reactions proceed via the intramolecular insertion of an olefin into a Pd(Ar)(OR) intermediate are discussed.

Entities:  

Year:  2004        PMID： 14871078     DOI： 10.1021/ja0394838

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  35 in total

1.  Intercepting Wacker intermediates with arenes: C-H functionalization and dearomatization.

Authors:  Bryan S Matsuura; Allison G Condie; Ian A McBee; Ryan C Buff; Gregory J Karahalis; Corey R J Stephenson
Journal:  Org Lett       Date:  2011-11-09       Impact factor: 6.005

2.  Copper-catalyzed intramolecular alkene carboetherification: synthesis of fused-ring and bridged-ring tetrahydrofurans.

Authors:  Yan Miller; Lei Miao; Azade S Hosseini; Sherry R Chemler
Journal:  J Am Chem Soc       Date:  2012-07-05       Impact factor: 15.419

3.  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

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.  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

6.  A new synthesis of imidazolidin-2-ones via Pd-catalyzed carboamination of N-allylureas.

Authors:  Jonathan A Fritz; Josephine S Nakhla; John P Wolfe
Journal:  Org Lett       Date:  2006-06-08       Impact factor: 6.005

7.  Two palladium-catalyzed domino reactions from one set of substrates/reagents: efficient synthesis of substituted indenes and cis-stilbenoid hydrocarbons from the same internal alkynes and hindered Grignard reagents.

Authors:  Cheng-Guo Dong; Pik Yeung; Qiao-Sheng Hu
Journal:  Org Lett       Date:  2007-01-18       Impact factor: 6.005

8.  Synthesis of polysubstituted tetrahydrofurans via Pd-catalyzed carboetherification reactions.

Authors:  Michael B Hay; John P Wolfe
Journal:  Tetrahedron Lett       Date:  2006-04-17       Impact factor: 2.415

9.  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

10.  Pd(OAc)(2)-catalyzed domino reactions of 1,2-dihaloarenes and 2-haloaryl arenesulfonates with Grignard reagents: efficient synthesis of substituted fluorenes.

Authors:  Cheng-Guo Dong; Qiao-Sheng Hu
Journal:  Tetrahedron       Date:  2008-03-10       Impact factor: 2.457
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