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A theoretical investigation on the mechanism of the α,α-diphenylprolinol trimethylsilyl ether-catalyzed oxyamination reaction

✍ Scribed by Chiong Teck Wong

Book ID: 104096096
Publisher: Elsevier Science
Year: 2009
Tongue: French
Weight: 167 KB
Volume: 50
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2008.12.012

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✦ Synopsis

A theoretical investigation on the reaction mechanism of a chiral prolinol silyl ether-catalyzed oxyamination reaction strongly suggests that the reaction proceeds via an enol intermediate and not via an enamine intermediate. The catalyst generates the enol and forms an enol-catalyst complex. Nitrosobenzene subsequently reacts with the enol-catalyst complex to afford the (S)-N-nitroso aldol product. The proposed mechanism is able to account for the experimentally observed enantioselectivity.

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