✦ LIBER ✦

Mechanism of halogen-catalyzed Mukaiyama aldol reactions: concerted or stepwise?

✍ Scribed by Li Wang; Ming Wah Wong

Book ID: 104095326
Publisher: Elsevier Science
Year: 2008
Tongue: French
Weight: 197 KB
Volume: 49
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2008.04.054

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✦ Synopsis

The halogen-catalyzed (I 2 , Br 2 , and Cl 2 ) 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 I 2 -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.

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