Sulfinimines of trifluoropyruvate: Novel intermediates for chiral non racemic α-trifluoromethyl α-amino acids

Tetrahedron Letters

Volumn 39, Issue 42, 1998, Pages 7771-7774

  Bravo, Pierfrancesco ^b   Crucianelli, Marcello ^a   Vergani, Barbara ^a   Zanda, Matteo ^a  

^a POLITECNICO DI MILANO   (Italy)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

ALANINE; ALPHA AMINO ACID; ESTER; HALIDE; IMINE; LEUCINE; PHENYLALANINE; PHOSPHORANE DERIVATIVE; PYRUVIC ACID DERIVATIVE; TRIFLUOROPYRUVIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHIRALITY; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032532234     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01698-0     Document Type: Article

References (34)

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19. 8. (a) Preliminary attempts to obtain the sulfinimines (S)-1 by the method of Davis (see Ref. 5) met with failure. In fact, reaction of lithium hexamethyldisilazane (LiHMDS) with menthyl sulfinate (-)-2 (see Scheme 1), followed by addition of ethyl trifluoropyruvate (with or without CsF) invariably produced complex mixtures of products.
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22. 3).
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24. (b) See also: Lefebvre, I. M.; Evans, S. A., Jr. J. Org. Chem. 1997, 62, 7532-7533 and references therein.
25. s)-6a from diisopropyl ether increased its e.e. to 99.9%.
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27. (b) Hulce, M.; Mallamo, J. P.; Frye, L. L.; Kogan, T. P.; Posner, G. H. Org. Synth. 1984, 64, 196-206.
28. 13. Stereochemistry of 6c was determined by X-ray diffraction. Full data will be reported in a full paper.
29. 14. In the latter case, it is worth noting that no reduction of the C=N bond of (S)-1b was detected by careful examination of the crude reaction mixture, in sharp contrast with the reactions between iso-propylmagnesium halides and N-alkoxycarbonyl imines of trifluoropyruvate, in which 40% of reduction occurs (Ref. 1).
30. 15. When commercially available THF or benzene stored on molecular sieves were used without preliminary distillation from sodium, the N-sulfinyl α-amino esters 6c-g obtained from alkylmagnesium halides were isolated with only 20-50% e.e. The reasons for this dramatic racemization are currently under investigation.
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