Stereoelectronic Features in Indium Mediated Allylation - Synthesis of Homoallylic Alcohols/ Amines and Their Transformations

Homoallylic alcohols and amines are fundamental building blocks for many biologically active compounds. The allylation of carbonyl compounds with allyl organometallic reagents constitutes a simple and straight forward approach for their synthesis. Allyl indium reagents have emerged as a reagent of choice for allylation of carbonyl compounds under both aqueous and non-aqueous conditions. However, in application of this approach for the synthesis of homoallylic alcohols/ amines from ketones/ imines, the lower electrophilicity of ketone/imine carbon makes the transfer of allyl group to ketone/imine carbon much more challenging. The ease of hydrolysis of imine to carbonyl compound and amine further add to the difficulties. The present work is aimed to unravel the regio- and diastereochemical aspects in indium mediated allylation of ketones bearing proton donor groups (OH, COOH) alpha to carbonyl moiety and imines derived from heterocycles like pyridine-2-imines, quinoline-2-imines and indole-3-imines. In selected cases the homoallylic alcohols have been subjected to iodine mediated cyclization to provide 2,3-diaryltetrahydrofuran and 3-hydroxy-3,4-dihydrofuran-2(5H)-one derivatives.

Product details

• Authors: Dr S Kumar, Dr. S Kumar, Dr Pervinde Kaur, Dr Pervinder Kaur, Dr. Pervinder Kaur, Pervinder Kaur, Kumar, Dr S Kumar, S. Kumar
• Publisher: LAP Lambert Academic Publishing
• Languages: English, German
• Product format: Paperback / Softback
• Released: 19.09.2011
• EAN: 9783845473925
• ISBN: 978-3-8454-7392-5
• No. of pages: 164
• Subject: Natural sciences, medicine, IT, technology > Chemistry > Organic chemistry