Asymmetric recognition of TRISPHAT anion. Unusually high difference in reactivity of the pseudoenantiomers of Cinchona alkaloids

Tetrahedron Letters

Volumn 39, Issue 27, 1998, Pages 4825-4828

  Lacour, Jérôme ^a   Ginglinger, Catherine ^a   Favarger, France ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CINCHONA ALKALOID; CINCHONIDINE;

ANALYTIC METHOD; ARTICLE; CATION EXCHANGE; DERIVATIZATION; DRUG CONFORMATION; DRUG SYNTHESIS; ENANTIOMER; MOLECULAR RECOGNITION; NONHUMAN;

EID: 0032474708     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00943-5     Document Type: Article

References (31)

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11. 4 For general articles on hexacoordinated phosphorus adducts, see: a) Cherkasov, R. A.; Polezhaeva, N. A. Uspekhi Khimii 1987, 56, 287-321; Russ. Chem. Rev. 1987, 56, 163-181;
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16. 6 Cinchona alkaloids has been used successfully for the resolution of tris(benzenediolato)arsenate anion: a) Rosenheim, A.; Plato, W. Chem. Ber. 1925, 58, 2000-2009;
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20. +, 5] designates a mixture of both diastereomeric salts.
21. 2) renders the procedure less practical and economical on a large scale.
22. +, (P)-5] and analogy with the tris(benzenediolato)arsenate anion, see ref. 6c.
23. 10 The lower solubility of 2 vs. 6 leads to an important precipitation of 2 (and salts [2, 5]) along with 6. See Table 1.
24. 2 are 24, 4.0, >250, >250, 0.06, 5.8, 0.07, 2.9 and 13.3 mM respectively.
25. +, 5] is observed.
26. 13 a) Kobayashi, N.; Iwai, K. J. Am. Chem. Soc. 1978, 100, 7071-7072;
27. b) references 2c and cited therein.
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