3.3.3- trifluoropyruvic acid, methyl ester

Enantioselective Friedel-Crafts alkylation reactions were performed between substituted indoles and methyl trifluoropyruvate, using a chiral nonracemic C2-symmetric 2,2 -bipyridyl copper triflate complex as catalyst. The active copper(II) catalyst was generated in situ. The corresponding 3,3,3-trifluoro-2-hydroxy-2-indolyl-propionic acid methyl esters were formed in good yield (up to 79%), and in up to 90% enantiomeric excess (eq 18). 

Pyrimido[4,5-6][l,4]thiazines (262) have been prepared by cyclocondensation of the aminothiols (260) with methyl trifluoropyruvate (261) in benzene (89KGS1492), or with 4-substituted 3-halo-2,4-dioxobutyric acid esters (263) at pH 2-5 in DMF to give 6-carbethoxy-7-acyl derivatives of 5H-pyrimido[4,5-6][l,4]thiazines (264) (Equations (38) and (39)). 

A/ -(Methoxycarbonyl)triphenyl-A -phosphane imidc reacts with methyl trifluoropyruvate to form methyl 3,3.3-trifluoro-2-[(methoxycarbonyl)imino]propanoate (34) in 95% yield. This convenient building block readily undergoes addition of nucleophiles, such as Grignard reagents. without competing side reactions at the ester group to form trifluoromethylated amino acids 35. ... 

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