Title
Stereoelectronic Features in Indium Mediated Allylation: Synthesis of Homoallylic Alcohols/ Amines and Their Transformations,Used
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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 nonaqueous 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 pyridine2imines, quinoline2imines and indole3imines. In selected cases the homoallylic alcohols have been subjected to iodine mediated cyclization to provide 2,3diaryltetrahydrofuran and 3hydroxy3,4dihydrofuran2(5H)one derivatives.
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