The addition of lithium salts of 0-alkyloximes to aldehydes: Synthesis of ß-keto ö-alkyloximes

Shimon Shatzmiller; Eliezer Bahar; Sorin Bercovici; Alexander Cohen; Gerhard Verdoorn

doi:10.1055/s-1990-26920

The addition of lithium salts of 0-alkyloximes to aldehydes: Synthesis of ß-keto ö-alkyloximes

Shimon Shatzmiller^*, Eliezer Bahar, Sorin Bercovici, Alexander Cohen, Gerhard Verdoorn

^*Corresponding author for this work

School of Chemistry

Tel Aviv University

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Abstract

Addition of lithium salts of oxime O-ethers to aldehydes affords the thermodynamically unfavored ^-hydroxy (Z)-O-alkyloximes. Oxidation of the hydroxy function with chromium trioxide/pyridine complex gives the ß-keto O-alkyloximes. Facile alkylation of the 1,3-dicarbonyl analogs is possible via their sodium or lithium salts.

Original language	English
Pages (from-to)	502-504
Number of pages	3
Journal	Synthesis (Germany)
Volume	1990
Issue number	6
DOIs	https://doi.org/10.1055/s-1990-26920
State	Published - 1990

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abstract = "Addition of lithium salts of oxime O-ethers to aldehydes affords the thermodynamically unfavored ^-hydroxy (Z)-O-alkyloximes. Oxidation of the hydroxy function with chromium trioxide/pyridine complex gives the {\ss}-keto O-alkyloximes. Facile alkylation of the 1,3-dicarbonyl analogs is possible via their sodium or lithium salts.",

author = "Shimon Shatzmiller and Eliezer Bahar and Sorin Bercovici and Alexander Cohen and Gerhard Verdoorn",

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T2 - Synthesis of ß-keto ö-alkyloximes

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AU - Bahar, Eliezer

AU - Bercovici, Sorin

AU - Cohen, Alexander

AU - Verdoorn, Gerhard

PY - 1990

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AB - Addition of lithium salts of oxime O-ethers to aldehydes affords the thermodynamically unfavored ^-hydroxy (Z)-O-alkyloximes. Oxidation of the hydroxy function with chromium trioxide/pyridine complex gives the ß-keto O-alkyloximes. Facile alkylation of the 1,3-dicarbonyl analogs is possible via their sodium or lithium salts.

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The addition of lithium salts of 0-alkyloximes to aldehydes: Synthesis of ß-keto ö-alkyloximes

Abstract

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