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|Title:||Mechanism of halogen-catalyzed Mukaiyama aldol reactions: concerted or stepwise?|
|Authors:||Wang, L. |
Wah Wong, M.
|Source:||Wang, L., Wah Wong, M. (2008-06-09). Mechanism of halogen-catalyzed Mukaiyama aldol reactions: concerted or stepwise?. Tetrahedron Letters 49 (24) : 3916-3920. ScholarBank@NUS Repository. https://doi.org/10.1016/j.tetlet.2008.04.054|
|Abstract:||The halogen-catalyzed (I2, Br2, and Cl2) Mukaiyama aldol (MA) reactions were investigated by ab initio MO calculations. The halogen-catalyzed MA reaction between a trihydrosilyl enol ether and formaldehyde favors a concerted pathway. In sharp contrast, the I2-catalyzed reaction between 1-phenyl-1-(trimethylsilyloxy)ethylene and benzaldehyde favors a stepwise mechanism. The nature of the substituent strongly influences the type of mechanism involved. © 2008 Elsevier Ltd. All rights reserved.|
|Source Title:||Tetrahedron Letters|
|Appears in Collections:||Staff Publications|
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