One-Pot Synthesis of α-Substituted Hydroxylamine Derivatives from Aldehydes Using Lithium Perchlorate/Diethyl Ether as a Catalyst

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

References

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13

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.