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We were first to demonstrate that Reformatsky-type additions between chiral N-sulfinylimines and ethyl bromodifluoroacetate affords an efficient approach for preparing the target β-substituted α,α- difluoro-α-amino acids 2; see ref 12 (Received: March 20, 2002). While the work on scope of this method was in progress, Staas et al. published their results on the asymmetric synthesis of amino acids 2, using N-tert-butylsulfinimines; see ref 13 (Received: May 13, 2002).
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2COOMe could be generated at room temperature by treating a methyl iododifluoroacetate with activated Zn powder; see ref 9a.
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49
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0141695724
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Besides the high temperature, as an unfavorable factor for achieving high diastereoselectivity in the addition reactions under study, the use of THF as a solvent was shown to result in reduced stereoselectivity as compared with the stereochemical outcome of the reactions conducted in diethyl ether; see refs 14c and 19.
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The procedures previously developed for determination of enantiomeric composition of various β-amino acids were used: Galushko, S. V.; Shishkina, I. P.; Soloshonok, V. A. J. Chromatogr. 1992, 592, 345. Racemic samples of amino acids 2a-e,g-i were prepared by the method described in this paper protocol, using racemic 4a-e,g-i as starting compounds.
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For various effects of fluorine and fluorine-containing substituents on the stereochemical outcome of the asymmetric reactions see ref 4c, as well as the following original papers: (a) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P. Tetrahedron 1996, 52, 12433-12442.
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84981828672
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The (S)-configuration of amino acids 2, a consequence of the Cahn - Ingold - Prelog priority, is stereochemically equivalent to the (R)-configuration in the hydrocarbon series: Cahn, R. S.; Ingold, C.; Prelog, V. Angew. Chem., Int. Ed. Engl. 1966, 5, 385.
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0141695723
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As suggested by the referee, the insignificant differences in the diastereoselectivity observed in the aliphatic series can be accounted for by the high-temperature reaction conditions required for these addition reactions.
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