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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 |
| Appears in Collections: | Staff Publications |
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