Please use this identifier to cite or link to this item:
|Title:||A new mechanistic proposal for the origin of α-homoallylic alcohols in indium-mediated allylation reactions in water|
|Authors:||Loh, T.-P. |
|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. 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|
|Appears in Collections:||Staff Publications|
Show full item record
Files in This Item:
There are no files associated with this item.
checked on Dec 11, 2018
WEB OF SCIENCETM
checked on Dec 3, 2018
checked on Nov 9, 2018
Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.