15925-47-0Relevant articles and documents
Solvent-free microwave-assisted organic reactions prepation of β-keto esters
Gianotti, Massimo,Martelli, Giorgio,Spunta, Giuseppe,Campana, Eileen,Panunrio, Mauro,Mendozza, Monica
, p. 1725 - 1730 (2000)
Microwave technique has been utilised in the preparation of β-keto esters. Two different procedures are described: transesterification of β- keto esters and ring opening of 2,2,6-trimethyl-1,3-dioxin-4-one.
An improved multigram-scale preparation of S-tertbutyl acetothioacetate
Lopez-Alvarado,Avendano,Menendez
, p. 2329 - 2333 (2007/10/02)
An efficient synthesis of S-tertbutylacetothioacetate was achieved by reaction between (t)butylthiol and 2,2,6-trimethyl-4H-1,3-dioxin-4-one.
PREPARATION OF ACYLTETRONIC ACIDS USING t-BUTYL ACETOTHIOACETATE: TOTAL SYNTHESIS OF THE FUNGAL METABOLITES CAROLIC, CARLOSIC, AND CARLIC ACIDS
Booth, Paul M.,Fox, Christina, M. J.,Ley, Steve V.
, p. 121 - 130 (2007/10/02)
Dianions generated from S-t-butyl acetothioacetate ( 1 ) were alkylated with a variety of electrophiles at the γ-carbon centre.Treatment of the alkylated products with 2-hydroxy esters in the presence of silver(I) salts gave transesterified acetoacetate derivatives in good yields.These acetoacetates were cyclised efficiently to acyltetronic acid derivatives using tetrabutyl ammonium fluoride in THF solution at room temperature.By an appropriate choice of substituents the total synthesis of the fungal metabolite natural products carlosic, carolic, and carlic acids have been achieved.
REGIOSPECIFIC ALKYLATION OF Β-KETOTHIOESTERS AND USE IN THE SYNTHESIS OF ACYL-TETRAONIC ACIDS
Booth, Paul M.,Fox, Christina M. J.,Ley, Steven V.
, p. 5143 - 5146 (2007/10/02)
Anions of t-butylacetothioacetate (1) react with alkylhalides and carbonyl compounds in a regiospecific manner to afford products which are versatile synthetic intermediates as exemplified by short syntheses of the mold metabolites carolic acid (2) and carlosic acid (3).
Acylations of Thiol Ester Enolate Anions
Wilson, G. Edwin,Hess, Arye
, p. 2766 - 2772 (2007/10/02)
The synthetic utility of thiol ester anions has been explored.Claisen condensations of thiol esters with isopropylmagnesium bromide base proceed in good yield.The Dieckmann reaction of diethyl thiolpimelate to form a six-membered ring proceeds in 74 percent yield, but the corresponding reaction of diethyl thioladipate to provide a five-membered ring gives only 26 percent yield.Neither alkylation of ethyl thiolacetate nor a Michael-type adduct with methyl vinyl ketone could be achieved.The mechanism of the Claisen condensation as it applies to thiol esters is discussed.
