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Our recent work has focused on the use of chiral, transition metalphosphine complexes to catalyze the addition of carbon based nucleophiles to imino esters (X = Ts) with high diastereo- and enantioselcctivity to yield protected amino acids S: (a) Ferraris, D.; Young, B. Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548-4549.
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The drawbacks of this synthetic methodology are the purification and hydrolytic lability of the imino 3 as well as the deprotection of the tosyl group after alkylation
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This reaction was not of interest to us and for this reason, the yields and selectivities were not optimized. For catalytic enantioselective alkylations of ethyl glyoxylate, see: (a) Evans, D. A.; Olhava, E. J.; Johnson, J. S.; Janey, J. M. Angew. Chem. Int. Ed. Eng. 1998, 37, 3372.
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