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Silyl enol ethers as new protecting groups for alkyl 4-halo-3-oxobutanoates; The preparation of pure (3-alkoxycarbonyl-2-oxopropyl)triphenylphosphonium salts
Citation
Moorhoff, CM, Silyl enol ethers as new protecting groups for alkyl 4-halo-3-oxobutanoates; The preparation of pure (3-alkoxycarbonyl-2-oxopropyl)triphenylphosphonium salts, Journal of the Chemical Society-Perkin Transactions, 1, (13) pp. 1987-1995. ISSN 0300-922X (1997) [Refereed Article]
DOI: doi:10.1039/a700241f
Abstract
A new method has been developed for the preparation of pure (3-alkoxycarbonyl-2-oxopropyl)triphenyl-phosphonium salts 8. Alkyl 4-bromo-3-oxobutanoates and alkyl 4-chloro-3-oxobutanoates 7 are protected as the trimethylsilyl enol ethers prior to treatment of the resulting bromo(trimethylsilyl enol ether) esters 20c and 21c with triphenylphosphine in toluene and then addition of a little water to give pure (3-isopropoxycarbonyl-2-oxopropyl)triphenylphosphonium bromide 8c. Bromo(silyl enol ether) esters react more efficiently with triphenylphosphine than the chloro(silyl enol ether) esters. tert-Butyldimethylsilyl enol ethers of alkyl 4-bromo-3-oxobutanoates and alkyl 4-chloro-3-oxobutanoates 7 also react with triphenylphosphine. Protection of isopropyl 4-bromo-3-oxobutanoate 7c as the enol acetate followed by subsequent reaction with triphenylphosphine gives (Z)-(2-acetoxy-3-isopropoxycarbonylbut-2-enyl)triphenylphosphonium bromide 17.
Item Details
Item Type: | Refereed Article |
---|---|
Research Division: | Chemical Sciences |
Research Group: | Organic chemistry |
Research Field: | Organic chemical synthesis |
Objective Division: | Expanding Knowledge |
Objective Group: | Expanding knowledge |
Objective Field: | Expanding knowledge in the chemical sciences |
UTAS Author: | Moorhoff, CM (Dr Moorhoff) |
ID Code: | 12012 |
Year Published: | 1997 |
Web of Science® Times Cited: | 8 |
Deposited By: | Chemistry |
Deposited On: | 1997-08-01 |
Last Modified: | 2011-08-15 |
Downloads: | 0 |
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