Lewis acid promoted, O-selective, nucleophilic addition of silyl enol ethers to N=O bonds

Norie Momiyama; Hisashi Yamamoto

doi:10.1002/1521-3773(20020816)41:16<2986::AID-ANIE2986>3.0.CO;2-F

Lewis acid promoted, O-selective, nucleophilic addition of silyl enol ethers to N=O bonds

Norie Momiyama, Hisashi Yamamoto

SCI - Chemistry

Research output: Contribution to journal › Article › peer-review

85 Citations (Scopus)

Abstract

Not N-adduct but O-adduct is formed in the Lewis acid catalyzed nucleophilic addition of silyl enol ethers 2 to the N=O bond of nitrosobenzene (1). Various Lewis acids (e.g. alkylsilyl triflates) efficiently catalyze the formation of the aminooxy ketone (O-adduct 3) rather than of the hydroxyamino ketone (N-adduct 4), which is the product of the uncatalyzed reaction.

Original language	English
Pages (from-to)	2986-2988
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	41
Issue number	16
DOIs	https://doi.org/10.1002/1521-3773(20020816)41:16<2986::AID-ANIE2986>3.0.CO;2-F
Publication status	Published - 2002 Aug 16

Keywords

Lewis acids
Nitroso compounds
Nucleophilic addition
Silyl enol ethers
Synthetic methods

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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AU - Yamamoto, Hisashi

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N2 - Not N-adduct but O-adduct is formed in the Lewis acid catalyzed nucleophilic addition of silyl enol ethers 2 to the N=O bond of nitrosobenzene (1). Various Lewis acids (e.g. alkylsilyl triflates) efficiently catalyze the formation of the aminooxy ketone (O-adduct 3) rather than of the hydroxyamino ketone (N-adduct 4), which is the product of the uncatalyzed reaction.

AB - Not N-adduct but O-adduct is formed in the Lewis acid catalyzed nucleophilic addition of silyl enol ethers 2 to the N=O bond of nitrosobenzene (1). Various Lewis acids (e.g. alkylsilyl triflates) efficiently catalyze the formation of the aminooxy ketone (O-adduct 3) rather than of the hydroxyamino ketone (N-adduct 4), which is the product of the uncatalyzed reaction.

KW - Lewis acids

KW - Nitroso compounds

KW - Nucleophilic addition

KW - Silyl enol ethers

KW - Synthetic methods

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Lewis acid promoted, O-selective, nucleophilic addition of silyl enol ethers to N=O bonds

Abstract

Keywords

ASJC Scopus subject areas

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