General Synthesis of Ketones from Carboxylic Esters and Carboxamides by Use of Mixed Organolithium‐Magnesium Reagents: Syntheses of Artemisia Ketone
- 4 November 1987
- journal article
- research article
- Published by Wiley in Helvetica Chimica Acta
- Vol. 70 (7), 1745-1752
- https://doi.org/10.1002/hlca.19870700710
Abstract
The novel reagents formed by combination of Grignard reagents (RMgX) with lithium diisopropylamide (LDA) convert non‐enolizable or slowly enolizable carboxylic esters or caboxamides into ketones which are protected from further reaction by their in situ conversion into enolates. These enolates can be trapped with electrophiles such as Me3SiCl and allyl bromide. The scope of this Grignard mono‐addition is illustrated by two direct syntheses of artemisia ketone (14).This publication has 21 references indexed in Scilit:
- The Hydrolysis of Ethyl 1-Methyl-2,4-cyclopentadiene-1-carboxylate by Nonenzymatic and Enzymatic Methods. Carbon-Carbonvs. Carbon-Oxygen Bond CleavageHelvetica Chimica Acta, 1987
- Enolate equilibria and force field parametersThe Journal of Organic Chemistry, 1987
- Acylation of organolithium reagents by esters in the presence of chlorotrimethylsilaneThe Journal of Organic Chemistry, 1986
- Synthese von β,γ‐ und α,β‐ungesättigten Ketonen mittels Allyltitan‐AgenzienEuropean Journal of Inorganic Chemistry, 1985
- Erste Synthese vonrac-Homofenchon (1,4,4-Trimethylbicyclo-[3.2.1]octan-3-on)European Journal of Organic Chemistry, 1985
- Stereoselective synthesis of (.+-.)-trichodieneThe Journal of Organic Chemistry, 1984
- Stereochemistry of an Ene Reaction Involving 1,7‐Dienes; Bicyclo[3.3.1]nonanes from (3‐Cyclohexenyl)diallylcarbinolsHelvetica Chimica Acta, 1984
- Condensation des Organomagnésiens sur les Chlorures D'Acide Dans le Tetrahydrofuranne a Basse TempératureBulletin des Sociétés Chimiques Belges, 1984
- Fragmentation of Homoallylic Alkoxides. Preparation of 1‐(3′‐cyclopentenyl)‐2‐alkanones from 2‐substituted bicyclo[2.2.1]hept‐5‐en‐2‐olsHelvetica Chimica Acta, 1983
- Fragmentation of Homoallylic Alkoxides. Thermolysis of potassium 2‐substituted bicyclo [2.2.2]oct‐5‐en‐2‐alkoxidesHelvetica Chimica Acta, 1981