Please use this identifier to cite or link to this item: https://doi.org/10.1016/j.tetlet.2008.04.054
Title: Mechanism of halogen-catalyzed Mukaiyama aldol reactions: concerted or stepwise?
Authors: Wang, L. 
Wah Wong, M. 
Issue Date: 9-Jun-2008
Citation: 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
URI: http://scholarbank.nus.edu.sg/handle/10635/94190
ISSN: 00404039
DOI: 10.1016/j.tetlet.2008.04.054
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