Literature DB >> 14535788

General method for the palladium-catalyzed allylation of aliphatic alcohols.

Anthony R Haight1, Eric J Stoner, Matthew J Peterson, Vandana K Grover.   

Abstract

A palladium catalysis-mediated approach to coupling aliphatic alcohols with allyl carbonates has been developed. The method allows for the allylation of primary, secondary, and tertiary alcohols efficiently under mild conditions. Limitations were explored as well as the asymmetric application of the chemistry. Regiochemical and olefin geometry was controlled in the coupling of unsymmetrical allylating agents. Transient allyl carbonates were observed in the coupling, which comprised the trans-carboxylation of the allyl-carbonate with the requisite alcohol.

Entities:  

Year:  2003        PMID： 14535788     DOI： 10.1021/jo0301907

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  9 in total

1.  Intramolecular hydrogen bonding: a potential strategy for more bioavailable inhibitors of neuronal nitric oxide synthase.

Authors:  Kristin Jansen Labby; Fengtian Xue; James M Kraus; Haitao Ji; Jan Mataka; Huiying Li; Pavel Martásek; Linda J Roman; Thomas L Poulos; Richard B Silverman
Journal:  Bioorg Med Chem       Date:  2012-02-07       Impact factor: 3.641

2.  Direct, iridium-catalyzed enantioselective and regioselective allylic etherification with aliphatic alcohols.

Authors:  Satoshi Ueno; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

3.  Improved synthesis of chiral pyrrolidine inhibitors and their binding properties to neuronal nitric oxide synthase.

Authors:  Fengtian Xue; James M Kraus; Kristin Jansen Labby; Haitao Ji; Jan Mataka; Guoyao Xia; Huiying Li; Silvia L Delker; Linda J Roman; Pavel Martásek; Thomas L Poulos; Richard B Silverman
Journal:  J Med Chem       Date:  2011-08-22       Impact factor: 7.446

4.  Pd-catalyzed cross-coupling of α-(acyloxy)-tri-n-butylstannanes with alkenyl, aryl, and heteroaryl electrophiles.

Authors:  Mohan Goli; Anyu He; J R Falck
Journal:  Org Lett       Date:  2010-12-09       Impact factor: 6.005

5.  Cyclic 1,2-diketones as core building blocks: a strategy for the total synthesis of (-)-terpestacin.

Authors:  Barry M Trost; Guangbin Dong; Jennifer A Vance
Journal:  Chemistry       Date:  2010-06-01       Impact factor: 5.236

6.  Gas-phase pyrolytic reaction of 4-aryl-3-buten-2-ols and allyl benzyl ethers: kinetic and mechanistic study.

Authors:  Alya M Al-Etaibi; Nouria A Al-Awadi; Maher R Ibrahim; Yehia A Ibrahim
Journal:  Molecules       Date:  2010-01-20       Impact factor: 4.411

7.  Metal Triflate-Promoted Allylic Substitution Reactions of Cinnamyl Alcohol in the Presence of Orthoesters and Acetals.

Authors:  Dawn R Chaffey; Carla Alamillo-Ferrer; Thomas E Davies; Stuart H Taylor; Nicholas C O Tomkinson; Andrew E Graham
Journal:  ACS Omega       Date:  2019-09-23

8.  Total synthesis of remdesivir.

Authors:  Kishore Kumar Palli; Palash Ghosh; Shiva Krishna Avula; B Sridhara Shanmukha Rao; Amol D Patil; Subhash Ghosh; Gangarajula Sudhakar; Chada Raji Reddy; Prathama S Mainkar; Srivari Chandrasekhar
Journal:  Tetrahedron Lett       Date:  2021-12-09       Impact factor: 2.415

9.  Synthetic methodology towards allylic trans-cyclooctene-ethers enables modification of carbohydrates: bioorthogonal manipulation of the lac repressor.

Authors:  Mark A R de Geus; G J Mirjam Groenewold; Elmer Maurits; Can Araman; Sander I van Kasteren
Journal:  Chem Sci       Date:  2020-09-08       Impact factor: 9.825
  9 in total

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