Literature DB >> 28436669

Stereoselective Synthesis of Exocyclic Tetrasubstituted Vinyl Halides via Ru-Catalyzed Halotropic Cycloisomerization of 1,6-Haloenynes.

Barry M Trost1, Christopher A Kalnmals1.   

Abstract

Herein, a ruthenium-catalyzed cycloisomerization that transforms 1,6-haloenynes into 5-membered carbo- and heterocycles that bear exocyclic, stereodefined, tetrasubstituted vinyl halides is reported. The reaction is insensitive to air and water, tolerates a variety of functional groups, and proceeds with good to excellent stereoselectivity and yield.

Entities:  

Mesh：

Substances：

Year:  2017        PMID： 28436669      PMCID： PMC5726863          DOI： 10.1021/acs.orglett.7b00879

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


  15 in total

Review 1.  Non-metathesis ruthenium-catalyzed C-C bond formation.

Authors:  B M Trost; F D Toste; A B Pinkerton
Journal:  Chem Rev       Date:  2001-07       Impact factor: 60.622

2.  Transition Metal-Catalyzed Carbocyclizations in Organic Synthesis.

Authors:  Iwao Ojima; Maria Tzamarioudaki; Zhaoyang Li; Robert J. Donovan
Journal:  Chem Rev       Date:  1996-03-28       Impact factor: 60.622

3.  Palladium-catalyzed intramolecular iodine-transfer reactions in the presence of β-hydrogen atoms.

Authors:  Brendan M Monks; Silas P Cook
Journal:  Angew Chem Int Ed Engl       Date:  2013-11-19       Impact factor: 15.336

Review 4.  Ruthenium-catalyzed reactions--a treasure trove of atom-economic transformations.

Authors:  Barry M Trost; Mathias U Frederiksen; Michael T Rudd
Journal:  Angew Chem Int Ed Engl       Date:  2005-10-21       Impact factor: 15.336

5.  cis-chloropalladation of 1,6-enynes.

Authors:  Gangguo Zhu; Zhaoguo Zhang
Journal:  J Org Chem       Date:  2005-04-15       Impact factor: 4.354

Review 6.  Metal-catalyzed cycloisomerization as a powerful tool in the synthesis of complex sesquiterpenoids.

Authors:  Christos I Stathakis; Petros L Gkizis; Alexandros L Zografos
Journal:  Nat Prod Rep       Date:  2016-08-25       Impact factor: 13.423

7.  Rhodium-catalyzed cycloisomerization of 1,6-enynes with an intramolecular halogen shift: reaction scope and mechanism.

Authors:  Xiaofeng Tong; Dao Li; Zhaoguo Zhang; Xumu Zhang
Journal:  J Am Chem Soc       Date:  2004-06-23       Impact factor: 15.419

8.  Efficient palladium-catalyzed coupling of aryl chlorides and tosylates with terminal alkynes: use of a copper cocatalyst inhibits the reaction.

Authors:  Dmitri Gelman; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2003-12-15       Impact factor: 15.336

9.  An atom-economic and selective ruthenium-catalyzed redox isomerization of propargylic alcohols. An efficient strategy for the synthesis of leukotrienes.

Authors:  Barry M Trost; Robert C Livingston
Journal:  J Am Chem Soc       Date:  2008-08-15       Impact factor: 15.419

10.  Mechanistic aspects of transition metal catalysed 1,6-diene and 1,6-enyne cycloisomerisation reactions.

Authors:  Guy C Lloyd-Jones
Journal:  Org Biomol Chem       Date:  2003-01-21       Impact factor: 3.876
View more
  2 in total

1.  A Convergent Synthesis of Functionalized Alkenyl Halides through Cobalt(III)-Catalyzed Three-Component C-H Bond Addition.

Authors:  Jeffrey A Boerth; Jonathan A Ellman
Journal:  Angew Chem Int Ed Engl       Date:  2017-07-17       Impact factor: 15.336

2.  Synthetic progress toward the marine natural product zamamiphidin A.

Authors:  Hao Wang; Di Tian; Zhaoxiang Meng; Zhihao Chen; Fei Xue; Xiao-Yu Liu; Hao Song; Yong Qin
Journal:  RSC Adv       Date:  2020-03-24       Impact factor: 4.036
  2 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.