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Synthesis 2003(13): 1962-1964
DOI: 10.1055/s-2003-41454
DOI: 10.1055/s-2003-41454
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York
One-Pot Synthesis of α-Substituted Hydroxylamine Derivatives from Aldehydes Using Lithium Perchlorate/Diethyl Ether as a Catalyst
Further Information
Received
5 May 2003
Publication Date:
10 September 2003 (online)
Publication History
Publication Date:
10 September 2003 (online)
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Abstract
O-(Trimethylsilyl)oxime ethers, generated in situ by reaction of aldehydes and O-(trimethylsilyl)hydroxylamine in lithium perchlorate/diethyl ether solution, are highly reactive species and undergo facile reaction with silylated nucleophiles, such as trimethylsilyl cyanide and the binary reagent (MeO)3P/Me3SiCl, to give α-substituted hydroxylamine derivatives.
Key words
lithium perchlorate - oximes - α-substituted hydroxylamines
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References
When a solution of aldehyde and O-(trimethylsilyl)hydroxyl-amine was treated with trimethyl phosphite/trimethylsilyl chloride in Et2O in the absence of LPDE at r.t. for 4 h, the corresponding O-(trimethylsilyl)oxime ether product was obtained in high yield.