Please use this identifier to cite or link to this item: https://doi.org/10.1016/S0040-4039(01)01884-6
Title: A new mechanistic proposal for the origin of α-homoallylic alcohols in indium-mediated allylation reactions in water
Authors: Loh, T.-P. 
Tan, K.-T. 
Hu, Q.-Y.
Issue Date: 3-Dec-2001
Source: 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. https://doi.org/10.1016/S0040-4039(01)01884-6
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/10635/75450
ISSN: 00404039
DOI: 10.1016/S0040-4039(01)01884-6
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