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Volumn , Issue 4, 2005, Pages 683-700

Mild protocols for generating molecular complexity: A comparative study of hetero-domino reactions based on the oxidant and the substitution pattern

Author keywords

Domino reactions; Glycol fission reagents; Ring expansion; Synthetic methods

Indexed keywords

BISMUTH DERIVATIVE; DIKETONE; GLYCOL; MANGANESE DERIVATIVE; OXIDIZING AGENT; PERIODINANE; PYRIDINIUM CHLOROCHROMATE; PYRIDINIUM DERIVATIVE; PYRIDINIUM DICHROMATE; SODIUM DERIVATIVE; TETRAPROPYLAMMONIUM; TETRAPROPYLAMMONIUM PERRUTHENATE; UNCLASSIFIED DRUG;

EID: 14944381486     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400549     Document Type: Article
Times cited : (15)

References (71)
  • 1
    • 33750173220 scopus 로고
    • Tietze proposed the following definition: "a domino reaction is a process involving two or more bond-forming transformations (usually C-C bonds) which take place under the same reaction conditions without adding additional reagents and catalysts, and in which the subsequent reactions result as a consequence of the functionality formed in the previous step." a) L. F. Tietze, U. Beifuss, Angew. Chem. Int. Ed. Engl. 1993, 32, 131-163;
    • (1993) Angew. Chem. Int. Ed. Engl. , vol.32 , pp. 131-163
    • Tietze, L.F.1    Beifuss, U.2
  • 4
    • 0001847186 scopus 로고    scopus 로고
    • (Eds.: M. Shibasaki, J. F. Stoddart, F. Vögtle), Wiley-VCH, Weinheim
    • d) L. F. Tietze, F. Haunert, in Stimulating Concepts in Chemistry (Eds.: M. Shibasaki, J. F. Stoddart, F. Vögtle), Wiley-VCH, Weinheim, 2000, p. 39-64.
    • (2000) Stimulating Concepts in Chemistry , pp. 39-64
    • Tietze, L.F.1    Haunert, F.2
  • 7
    • 0003757056 scopus 로고
    • (Ed.: K. B. Wiberg), Part A, Academic Press, New York
    • c) R. Criegee, in Oxidation in Organic Chemistry (Ed.: K. B. Wiberg), Part A, Academic Press, New York, 1965, p. 277.
    • (1965) Oxidation in Organic Chemistry , pp. 277
    • Criegee, R.1
  • 14
    • 0001301163 scopus 로고    scopus 로고
    • For routes to gain synthetic entry to systems containing seven-membered ring, see: P. A. Wender, A. J. Dyckman, C. O. Husfeld, M. J. C. Scanio, Org. Lett. 2000, 2, 1609-1611; P. A. Wender, A. J. Dyckman, C. O. Husfeld, M. J. C. Scanio, Org. Lett. 2001, 3, 2105-2108 and references cited therein.
    • (2000) Org. Lett. , vol.2 , pp. 1609-1611
    • Wender, P.A.1    Dyckman, A.J.2    Husfeld, C.O.3    Scanio, M.J.C.4
  • 15
    • 0035963703 scopus 로고    scopus 로고
    • and references cited therein
    • For routes to gain synthetic entry to systems containing seven-membered ring, see: P. A. Wender, A. J. Dyckman, C. O. Husfeld, M. J. C. Scanio, Org. Lett. 2000, 2, 1609-1611; P. A. Wender, A. J. Dyckman, C. O. Husfeld, M. J. C. Scanio, Org. Lett. 2001, 3, 2105-2108 and references cited therein.
    • (2001) Org. Lett. , vol.3 , pp. 2105-2108
    • Wender, P.A.1    Dyckman, A.J.2    Husfeld, C.O.3    Scanio, M.J.C.4
  • 34
    • 0030013187 scopus 로고    scopus 로고
    • For the precursor of 13a, the corresponding angularly functionalized octaline dione, the method of Benn and Hanselmann (L-proline, DMSO, room temp.) was used, R. Hanselmann, M. Benn, Synth. Commun. 1996, 26, 945-961.
    • (1996) Synth. Commun. , vol.26 , pp. 945-961
    • Hanselmann, R.1    Benn, M.2
  • 37
    • 14944361920 scopus 로고    scopus 로고
    • note
    • [l7] "the first stereogenic center must be introduced catalytically, and the process must be elegant, efficient, and non-polluting".[1]
  • 44
    • 0027988788 scopus 로고
    • a) M. Frigerio, M. Santagostino, Tetrahedron Lett. 1994, 35, 8019. DMP is best prepared using the Santagostino procedure (OXONE® oxidation) for the first step, the IBX formation, and the Ireland protocol for the second, instead of using the original Dess-Martin procedure,
    • (1994) Tetrahedron Lett. , vol.35 , pp. 8019
    • Frigerio, M.1    Santagostino, M.2
  • 61
    • 1542432680 scopus 로고
    • (Ed.: K. B. Wiberg); Academic Press, New York
    • K. B. Wiberg, in Oxidation in Organic Chemistry (Ed.: K. B. Wiberg); Academic Press, New York. 1965, Part A, pp. 170-172.
    • (1965) Oxidation in Organic Chemistry , Issue.PART A , pp. 170-172
    • Wiberg, K.B.1
  • 68
    • 14944358256 scopus 로고    scopus 로고
    • note
    • Oxidation of alkenes by lead tetraacetate on heating is well known; the olefin remains unaltered at room temperature.
  • 69
    • 14944351515 scopus 로고    scopus 로고
    • note
    • In no case was the ring-expanded product detected in the reaction mixtures employing oxidants known to promote glycol fission, including iodobenzene diacetate, though we cannot rule out their production in very minor amounts upon prolonged heating at reflux with the latter oxidant.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.