Literature DB >> 33418882

Modern Synthetic Methods for the Stereoselective Construction of 1,3-Dienes.

Raquel G Soengas1, Humberto Rodríguez-Solla1.   

Abstract

The <span class="Chemical">1,3-butadienen> motif is widely found in many natural products and d<span class="Chemical">rug candidates with relevant biological activities. Moreover, <span class="Chemical">dienes are important targets for synthetic chemists, due to their ability to give access to a wide range of functional group transformations, including a broad range of C-C bond-forming processes. Therefore, the stereoselective preparation of dienes have attracted much attention over the past decades, and the search for new synthetic protocols continues unabated. The aim of this review is to give an overview of the diverse methodologies that have emerged in the last decade, with a focus on the synthetic processes that meet the requirements of efficiency and sustainability of modern organic chemistry.

Entities:  

Keywords:  1,3-dienes; cross-coupling; dienylation; olefin metathesis

Mesh:

Substances:

Year:  2021        PMID: 33418882      PMCID: PMC7825119          DOI: 10.3390/molecules26020249

Source DB:  PubMed          Journal:  Molecules        ISSN: 1420-3049            Impact factor:   4.411


  166 in total

Review 1.  From α-arylation of olefins to acylation with aldehydes: a journey in regiocontrol of the Heck reaction.

Authors:  Jiwu Ruan; Jianliang Xiao
Journal:  Acc Chem Res       Date:  2011-05-25       Impact factor: 22.384

2.  Regio- and stereoselective synthesis of 2-amino-dienes via decarboxylative amination of 4-(ethoxycarbonyl)-2,3-allenols by TsNCO.

Authors:  Lijun Wu; Hui Huang; Yun Liang; Pi Cheng
Journal:  J Org Chem       Date:  2014-11-03       Impact factor: 4.354

3.  Synthesis of Chiral 1,3-Dienes through Ring-Closing Metathesis of Enantioenriched Enynes: Potential Precursors of Morphane Analogs.

Authors:  María Jesús Garcia-Muñoz; Ana Sirvent; Francisco Foubelo; Miguel Yus
Journal:  An Acad Bras Cienc       Date:  2018       Impact factor: 1.753

4.  Pd-catalyzed intramolecular C-N bond cleavage, 1,4-migration, sp3 C-H activation, and Heck reaction: four controllable diverse pathways depending on the judicious choice of the base and ligand.

Authors:  Min Wang; Xiang Zhang; Yu-Xuan Zhuang; Yun-He Xu; Teck-Peng Loh
Journal:  J Am Chem Soc       Date:  2015-01-15       Impact factor: 15.419

5.  Palladium(II)-catalyzed dehydrogenative alkenylation of cyclic enaminones via the Fujiwara-Moritani reaction.

Authors:  Yi-Yun Yu; Micah J Niphakis; Gunda I Georg
Journal:  Org Lett       Date:  2011-10-13       Impact factor: 6.005

6.  Up the hill: selective double-bond isomerization of terminal 1,3-dienes towards Z-1,3-dienes or 2Z,4E-dienes.

Authors:  Florian Pünner; Anastasia Schmidt; Gerhard Hilt
Journal:  Angew Chem Int Ed Engl       Date:  2011-12-15       Impact factor: 15.336

7.  Ruthenium- and rhodium-catalyzed cross-coupling reaction of acrylamides with alkenes: efficient access to (Z,E)-dienamides.

Authors:  Jian Zhang; Teck-Peng Loh
Journal:  Chem Commun (Camb)       Date:  2012-10-15       Impact factor: 6.222

8.  Design and Preparation of New Palladium Precatalysts for C-C and C-N Cross-Coupling Reactions.

Authors:  Nicholas C Bruno; Matthew T Tudge; Stephen L Buchwald
Journal:  Chem Sci       Date:  2013       Impact factor: 9.825

9.  Iridium-Catalyzed Cross-Coupling Reactions of Alkenes by Hydrogen Transfer.

Authors:  Keke Meng; Yaling Sun; Jian Zhang; Kaiyun Zhang; Xiaohui Ji; Liyuan Ding; Guofu Zhong
Journal:  Org Lett       Date:  2019-10-07       Impact factor: 6.005

10.  Highly Regio- and Stereoselective Catalytic Synthesis of Conjugated Dienes and Polyenes.

Authors:  Vu T Nguyen; Hang T Dang; Hoang H Pham; Viet D Nguyen; Carsten Flores-Hansen; Hadi D Arman; Oleg V Larionov
Journal:  J Am Chem Soc       Date:  2018-06-26       Impact factor: 15.419

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  1 in total

1.  A Dual CuH- and Pd-Catalyzed Stereoselective Synthesis of Highly Substituted 1,3-Dienes.

Authors:  Chuan-Jin Hou; Alexander W Schuppe; James Levi Knippel; Anton Z Ni; Stephen L Buchwald
Journal:  Org Lett       Date:  2021-11-02       Impact factor: 6.072

  1 in total

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