On the acylation reactions of aza-allyl carbanions derived from N-[bis(methylthio)methylene]glycine ethyl ester and N-[bis(methylthio)methylene]benzylamine

Tetrahedron

Volumn 53, Issue 10, 1997, Pages 3679-3692

  Alvarez Ibarra, Carlos ^a   Csákÿ, Aurelio G ^a   Martinez Santos, Elena ^a   Quiroga, María L ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

OXAZOLE DERIVATIVE; PYRROLE DERIVATIVE;

ACYLATION; ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031562463     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00091-4     Document Type: Article

References (37)

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5. 3 Hoppe and co-workers have described the first utilizations of N-[Bis(methylthio)methylene]glycine ester enolate as glycine nucleophile. The representative articles are as follows: (a) Hoppe, D. 1975. Angew. Chem. Int. Ed. Engl. 14, 424. (b) Hoppe, D.; Beckmann, L. 1979. Liebigs Ann. Chem. 2066.
6. 3 Hoppe and co-workers have described the first utilizations of N-[Bis(methylthio)methylene]glycine ester enolate as glycine nucleophile. The representative articles are as follows: (a) Hoppe, D. 1975. Angew. Chem. Int. Ed. Engl. 14, 424. (b) Hoppe, D.; Beckmann, L. 1979. Liebigs Ann. Chem. 2066.
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22. 9 A 7-analogue with an E configuration has been obtained by trifluoracetylation of hippuric acid: Cufos, T.; Diaz, P.; Stalk, L. Synlett 1995, 101. This α,β-didehydro-α-amino acid acts as a 2π-partner in a Diels-Alder cycloaddition with cyclopentadiene, which constitutes a relevant application because of the role of the α-quaternized α-amino acids in peptide-based drug design. Selected recent monographies or articles about asymmetric syntheses of α,α-quaternized α-amino acids are reported in: Goodman, M. R. S.; Wolff, M. E. (Eds). Burger's Medicinal Chemistry and Drug Discovery, John Wiley&Sons, Inc.: New York, 5th edition, 1994, Vol. 1, Chapter 25, pp. 803-861.
23. 9 A 7-analogue with an E configuration has been obtained by trifluoracetylation of hippuric acid: Cufos, T.; Diaz, P.; Stalk, L. Synlett 1995, 101. This α,β-didehydro-α-amino acid acts as a 2π-partner in a Diels-Alder cycloaddition with cyclopentadiene, which constitutes a relevant application because of the role of the α-quaternized α-amino acids in peptide-based drug design. Selected recent monographies or articles about asymmetric syntheses of α,α-quaternized α-amino acids are reported in: Goodman, M. R. S.; Wolff, M. E. (Eds). Burger's Medicinal Chemistry and Drug Discovery, John Wiley&Sons, Inc.: New York, 5th edition, 1994, Vol. 1, Chapter 25, pp. 803-861.
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36. 18 The syn-anti nomenclature has been used as proposed by Masamune. The chain containing the two asymmetryc centers is drawn in zig-zag fashion. In the syn isomers, both prioritary substituents of the stereogenic centers are directed either towards or away from the viewer. See: Masamune, S.; Ali, S. A.; Snitman, D. L.; Garvey, D. S. Angew. Chem., Int. Ed. Engl. 1980, 19, 557.
37. 19 The ul-lk notation has been used as proposed by Seebach and Prelog. It refers to two alternative approximations between the two diastereotopic faces of each one of the two functional groups involved in the reaction. A different topicity as re si is named ul, whereas for the same topicity as re re/re lk is used. See: Seebach, D.; Prelog, V. Angew. Chem., Int. Ed. Engl. 1982, 21, 654.