Literature DB >> 16506731

An alkoxide-directed carbometalation of internal alkynes.

Jamie Ryan1, Glenn C Micalizio.   

Abstract

A mild and efficient alkoxide-directed carbometalation is described. Regioselective carbon-carbon bond formation occurs in all cases at the site distal to the tethered alkoxide. This reaction provides a convenient means to prepare differentially functionalized tetrasubstituted 1,3-dienes in a regio- and stereoselective manner.

Entities:  

Year:  2006        PMID: 16506731     DOI: 10.1021/ja057352w

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


  28 in total

1.  Dative Directing Group Effects in Ti-Catalyzed [2+2+1] Pyrrole Synthesis: Chemo- and Regioselective Alkyne Heterocoupling.

Authors:  Hsin-Chun Chiu; Xin Yi See; Ian A Tonks
Journal:  ACS Catal       Date:  2018-11-29       Impact factor: 13.084

2.  Iron-catalyzed carbometalation of propargylic and homopropargylic alcohols.

Authors:  Donghui Zhang; Joseph M Ready
Journal:  J Am Chem Soc       Date:  2006-11-29       Impact factor: 15.419

3.  Reaction design, discovery, and development as a foundation to function-oriented synthesis.

Authors:  Glenn C Micalizio; Sarah B Hale
Journal:  Acc Chem Res       Date:  2015-02-10       Impact factor: 22.384

4.  Regio- and stereoselective cross-coupling of substituted olefins and imines. A convergent stereoselective synthesis of saturated 1,5-amino-alcohols and substituted piperidines.

Authors:  Masayuki Takahashi; Glenn C Micalizio
Journal:  J Am Chem Soc       Date:  2007-05-26       Impact factor: 15.419

5.  Synthesis of substituted 1,4-dienes by direct alkylation of allylic alcohols.

Authors:  Filip Kolundzic; Glenn C Micalizio
Journal:  J Am Chem Soc       Date:  2007-11-16       Impact factor: 15.419

6.  Recent Progress in Steroid Synthesis Triggered by the Emergence of New Catalytic Methods.

Authors:  Hem Raj Khatri; Nolan Carney; Ryan Rutkoski; Bijay Bhattarai; Pavel Nagorny
Journal:  European J Org Chem       Date:  2020-01-01

7.  Synthesis of Angularly Substituted trans-Fused Decalins through a Metallacycle-Mediated Annulative Cross-Coupling Cascade.

Authors:  Haruki Mizoguchi; Glenn C Micalizio
Journal:  Angew Chem Int Ed Engl       Date:  2016-10-10       Impact factor: 15.336

8.  Synthesis of Highly Functionalized Decalins via Metallacycle-Mediated Cross-Coupling.

Authors:  Haruki Mizoguchi; Glenn C Micalizio
Journal:  J Am Chem Soc       Date:  2015-05-12       Impact factor: 15.419

9.  Synthesis of the Cortistatin Pentacyclic Core by Alkoxide-Directed Metallacycle-Mediated Annulative Cross-Coupling.

Authors:  Claudio Aquino; Stephen N Greszler; Glenn C Micalizio
Journal:  Org Lett       Date:  2016-05-19       Impact factor: 6.005

10.  Allene-alkyne cross-coupling for stereoselective synthesis of substituted 1,4-dienes and cross-conjugated trienes.

Authors:  Heidi L Shimp; Alissa Hare; Martin McLaughlin; Glenn C Micalizio
Journal:  Tetrahedron       Date:  2008-04-14       Impact factor: 2.457

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