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Stereoelectronic Features in Indium Mediated Allylation

Dr. Pervinder Kaur

ISBN 10: 3845473924 / ISBN 13: 9783845473925
Published by LAP LAMBERT Academic Publishing
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Paperback. 164 pages. Dimensions: 8.7in. x 5.9in. x 0.4in.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 ketoneimine carbon makes the transfer of allyl group to ketoneimine 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. This item ships from multiple locations. Your book may arrive from Roseburg,OR, La Vergne,TN. Bookseller Inventory # 9783845473925

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Bibliographic Details

Title: Stereoelectronic Features in Indium Mediated...

Publisher: LAP LAMBERT Academic Publishing

Binding: Paperback

Book Condition:New

Book Type: Paperback

About this title

Synopsis:

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.

About the Author:

Dr.Pervinder Kaur, Ph.D: Chemistry from Guru Nanak Dev University, Assistant Professor, Department of Chemistry, Mata Ganga Khalsa College, Manji Sahib, Distt Ludhiana, Punjab,India.

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