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|Title:||A new mechanistic proposal for the origin of α-homoallylic alcohols in indium-mediated allylation reactions in water||Authors:||Loh, T.-P.
|Issue Date:||3-Dec-2001||Citation:||Loh, T.-P., Tan, K.-T., Hu, Q.-Y. (2001-12-03). A new mechanistic proposal for the origin of α-homoallylic alcohols in indium-mediated allylation reactions in water. Tetrahedron Letters 42 (49) : 8705-8708. ScholarBank@NUS Repository.||Abstract:||A new mechanism is proposed for the α-regioselective indium-mediated allylation reaction in water. Based on the results and observations obtained from an NMR study, a cross-over experiment and the complete inversion of the stereochemistry of 22β γ-adduct homoallylic sterols to the 22α α-adduct homoallylic sterols, it is suggested that the initially formed γ-adduct undergoes a bond cleavage to generate the parent aldehyde in situ followed by a concerted rearrangement, perhaps a retro-ene reaction followed by a 2-oxonia [3,3]-sigmatropic rearrangement to furnish the α-adduct. © 2001 Elsevier Science Ltd. All rights reserved.||Source Title:||Tetrahedron Letters||URI:||http://scholarbank.nus.edu.sg/handle/10635/92963||ISSN:||00404039|
|Appears in Collections:||Staff Publications|
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