Concepedia

A NEW METHOD FOR THE PREPARATION OF β-HYDROXYESTERS. THE TITANIUM TETRACHLORIDE-PROMOTED REACTION OF KETENE ALKYL TRIALKYLSILYL ACETALS WITH CARBONYL COMPOUNDS

Kazuhiko Saigo, Masaaki Osaki, Teruaki Mukaiyama

Chemistry Letters · 1975 · 71 citations · 5 references

DOI

Concepts

Abstract

Abstract In the presence of TiCl4, ketene alkyl trialkylsilyl acetals, prepared from α-lithio esters and a trialkylsilyl halide, react with aldehydes and ketones at −78°C to afford the corresponding β-hydroxyesters and β-trialkylsiloxyesters in good yields.

References

5

New cross-aldol reactions. Reactions of silyl enol ethers with carbonyl compounds activated by titanium tetrachloride

Teruaki Mukaiyama, Kazuo Banno, Koichi Narasaka · Journal of the American Chemical Society · 1974 · 803 citations

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O-Silylation and Attempted O-Alkylation of Lithium Ester Enolates. The Synthesis of O-Silyl Ketene Acetals

Michael W. Rathke, Donald F. Sullivan · Synthetic Communications · 1973 · 122 citations

, , +5

Preparation of lithio ethyl acetate. Procedure for the conversion of aldehydes and ketones to .beta.-hydroxy esters

Michael W. Rathke · Journal of the American Chemical Society · 1970 · 118 citations

, , +4

Synthesis of .beta.-hydroxy acids using .alpha.-lithiated carboxylic acid salts

G. W. Moersch, Allan R. Burkett · The Journal of Organic Chemistry · 1971 · 56 citations

, , +11

Reactions of Vinyloxyboranes. A Convenient Method for the Preparation of β-Hydroxy Thiolesters, Esters and Ketones

Katsuhiko Inomata, Masayoshi MURAKI, Teruaki Mukaiyama · Bulletin of the Chemical Society of Japan · 1973 · 52 citations · Full text

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