Literature DB >> 18046462

Absence of the Thorpe-Ingold Effect by gem-Diphenyl Groups in Ring-Closing Enyne Metathesis.

Yi Jin Kim1, Jonathan B Grimm, Daesung Lee.   

Abstract

In tandem ring-closing metathesis of alkynyl silaketals containing two different tethered olefins, the gem-dimethyl group showed the expected Thorpe-Ingold effect, thereby giving good level of group selectivity. Unexpectedly, however, the corresponding gem-diphenyl group did not show any Thorpe-Ingold effect for the ring closure reaction.

Entities:  

Year:  2007        PMID: 18046462      PMCID: PMC2097962          DOI: 10.1016/j.tetlet.2007.09.063

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


  15 in total

1.  Novel synthesis of heterocycles having a functionalized carbon center via nickel-mediated carboxylation: total synthesis of erythrocarine.

Authors:  Kazuya Shimizu; Masanori Takimoto; Miwako Mori
Journal:  Org Lett       Date:  2003-06-26       Impact factor: 6.005

2.  Formal synthesis of (+/-)-guanacastepene A: a tandem ring-closing metathesis approach.

Authors:  François-Didier Boyer; Issam Hanna; Louis Ricard
Journal:  Org Lett       Date:  2004-05-27       Impact factor: 6.005

Review 3.  Enyne metathesis (enyne bond reorganization).

Authors:  Steven T Diver; Anthony J Giessert
Journal:  Chem Rev       Date:  2004-03       Impact factor: 60.622

4.  Asymmetric total synthesis of rollicosin.

Authors:  Kevin J Quinn; André K Isaacs; Brian A DeChristopher; Stephanie C Szklarz; Rebecca A Arvary
Journal:  Org Lett       Date:  2005-03-31       Impact factor: 6.005

Review 5.  gem-disubstituent effect: theoretical basis and synthetic applications.

Authors:  Michael E Jung; Grazia Piizzi
Journal:  Chem Rev       Date:  2005-05       Impact factor: 60.622

6.  Synthesis and activity of a new generation of ruthenium-based olefin metathesis catalysts coordinated with 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene ligands.

Authors:  M Scholl; S Ding; C W Lee; R H Grubbs
Journal:  Org Lett       Date:  1999-09-23       Impact factor: 6.005

7.  Search for solutions to the reactivity and selectivity problems in enyne metathesis.

Authors:  Eric C Hansen; Daesung Lee
Journal:  Acc Chem Res       Date:  2006-08       Impact factor: 22.384

8.  Mechanism of enyne metathesis catalyzed by Grubbs ruthenium-carbene complexes: a DFT study.

Authors:  Jörg J Lippstreu; Bernd F Straub
Journal:  J Am Chem Soc       Date:  2005-05-25       Impact factor: 15.419

9.  Efficient synthesis of alkynylsilyl ethers and silaketals via base-induced alkynylsilane alcoholysis.

Authors:  Jonathan B Grimm; Daesung Lee
Journal:  J Org Chem       Date:  2004-12-10       Impact factor: 4.354

10.  Group-selective ring-closing enyne metathesis: concentration-dependent selectivity profile of alkynylsilyloxy-tethered dienynes.

Authors:  Sarah V Maifeld; Reagan L Miller; Daesung Lee
Journal:  J Am Chem Soc       Date:  2004-10-06       Impact factor: 15.419

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  1 in total

1.  A relay ring-closing metathesis synthesis of dihydrooxasilines, precursors of (Z)-iodo olefins.

Authors:  Qiuzhe Xie; Richard W Denton; Kathlyn A Parker
Journal:  Org Lett       Date:  2008-12-04       Impact factor: 6.005

  1 in total

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