✦ LIBER ✦

Highly regio- and chemoselective palladium(0)-mediated allylic substitution of difunctional allylic halides with phenols

✍ Scribed by Anant R. Kapdi; Richard J.K. Taylor; Ian J.S. Fairlamb

Publisher: Elsevier Science
Year: 2010
Tongue: French
Weight: 210 KB
Volume: 51
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2010.09.125

No coin nor oath required. For personal study only.

✦ Synopsis

An efficient Pd(0)-mediated, base-assisted reaction of phenols with difunctionalised allylic halides results in the formation of coupled products in good yields. The reactions proceed with excellent stereo-, regioand chemocontrol. An appropriately functionalised Weinreb amide, synthesised by this methodology, undergoes halogen-lithium exchange and subsequent intramolecular 1,2-carbonyl addition/elimination to give an advanced macrocyclic intermediate with potential use in the synthesis of likonide B.

📜 SIMILAR VOLUMES

Highly Substituted Homoallylvinylcyclopr

Highly Substituted Homoallylvinylcyclopropanes by Indium-Mediated Reaction of α,β-Unsaturated Ketones and Aldehydes with Allylic Halides

✍ Stephen M. Capps; Timothy P. Clarke; Jonathan P. H. Charmant; Henning A. F. Höpp 📂 Article 📅 2000 🏛 John Wiley and Sons 🌐 English ⚖ 477 KB 👁 1 views

Allylindium reagents, prepared from excess allylic halide (Br or I) and indium metal, react with α,β-unsaturated ketones and aldehydes to give, after aerobic acidic workup, homoallyl-substituted vinylcyclopropanes. This process was explored and developed after a chance discovery arising from a side

ChemInform Abstract: Highly Substituted

ChemInform Abstract: Highly Substituted Homoallylvinylcyclopropanes by Indium-Mediated Reaction of α,β-Unsaturated Ketones and Aldehydes with Allylic Halides.

✍ Stephen M. Capps; Timothy P. Clarke; Jonathan P. H. Charmant; Henning A. F. Hoep 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 34 KB 👁 1 views

Regio- and stereoselective palladium(0)-

Regio- and stereoselective palladium(0)-catalyzed alkylation of vinyloxiranes with non-stabilized lithium ester enolates nucleophiles. A direct access to highly functionalized allylic alcohols

✍ Maryse Rychlet Elliott; Anne-Lise Dhimane; Max Malacria 📂 Article 📅 1998 🏛 Elsevier Science 🌐 French ⚖ 230 KB

Recently, we reported an efficient palladium(0) catalyzed allylation of a non-stabilized nucleophile, lithium enolate of ethyl isobutyrate 2a, with monoepoxide of isoprene la, as a first step in the total synthesis of epiilludol (scheme 1).] The synthetic value of the regio-and stereoselective allyl

ChemInform Abstract: Synthesis of Highly

ChemInform Abstract: Synthesis of Highly Substituted Allylic Alcohols by a Regio- and Stereo-Defined CuCl-Mediated Carbometallation Reaction of 3-Aryl-Substituted Secondary Propargylic Alcohols with Grignard Reagents.

✍ Xiaobing Zhang; Zhan Lu; Chunling Fu; Shengming Ma 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 74 KB 👁 2 views

ChemInform Abstract: Regio- and Stereose

ChemInform Abstract: Regio- and Stereoselective Palladium(0)-Catalyzed Alkylation of Vinyloxiranes with Non-Stabilized Lithium Ester Enolates Nucleophiles. A Direct Access to Highly Functionalized Allylic Alcohols.

✍ M. R. ELLIOTT; A.-L. DHIMANE; M. MALACRIA 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 31 KB 👁 1 views