Literature DB >> 15128252

Highly regioselective ring-opening/cross-metathesis reactions of 2-sulfonylnorbornene derivatives.

G Mahika Weeresakare1, Zhuqing Liu, Jon D Rainier.   

Abstract

Tandem ring-opening/cross-metathesis (ROM/CM) reactions of norbornenes can be a powerful entry into highly substituted organic molecules. However, their utility has been limited largely to symmetrical norbornenes because of the general lack of regioselective variants of these reactions. This manuscript describes our successful attempts to address this issue through the use of a sulfone to direct the ROM/CM reaction of a 7-azanorbornene and a 7-oxanorbornene.

Entities:  

Year:  2004        PMID: 15128252     DOI: 10.1021/ol049561b

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  6 in total

1.  Enol ethers as substrates for efficient Z- and enantioselective ring-opening/cross-metathesis reactions promoted by stereogenic-at-Mo complexes: utility in chemical synthesis and mechanistic attributes.

Authors:  Miao Yu; Ismail Ibrahem; Masayuki Hasegawa; Richard R Schrock; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2012-01-24       Impact factor: 15.419

2.  Regioselective Domino Metathesis of Unsymmetrical 7-Oxanorbornenes with Electron-Rich Vinyl Acetate toward Biologically Active Glutamate Analogues.

Authors:  Masato Oikawa; Minoru Ikoma; Makoto Sasaki; Martin B Gill; Geoffrey T Swanson; Keiko Shimamoto; Ryuichi Sakai
Journal:  European J Org Chem       Date:  2009-11-01

3.  Enantioselective synthesis of 2,2,5-tri- and 2,2,5,5-tetrasubstituted tetrahydrofurans via [4 + 2] cycloaddition and ring-opening cross-metathesis.

Authors:  Noah M Benjamin; Stephen F Martin
Journal:  Org Lett       Date:  2011-01-06       Impact factor: 6.005

4.  Regioselective Domino Metathesis of 7-Oxanorbornenes and Its Application to the Synthesis of Biologically Active Glutamate Analogues.

Authors:  Minoru Ikoma; Masato Oikawa; Martin B Gill; Geoffrey T Swanson; Ryuichi Sakai; Keiko Shimamoto; Makoto Sasaki
Journal:  European J Org Chem       Date:  2008-11

5.  Synthesis of High Oxidation State Molybdenum Imido Heteroatom-Substituted Alkylidene Complexes.

Authors:  Erik M Townsend; Stefan M Kilyanek; Richard R Schrock; Peter Müller; Stacey J Smith; Amir H Hoveyda
Journal:  Organometallics       Date:  2013-08-26       Impact factor: 3.876

6.  The tandem ring opening/ring closing metathesis route to oxaspirocycles: an approach to phelligridin G.

Authors:  Harold D Cooper; Dennis L Wright
Journal:  Molecules       Date:  2013-02-21       Impact factor: 4.411

  6 in total

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