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Volumn 67, Issue 27-28, 2011, Pages 5046-5053

Heterocycles via intramolecular platinum-catalyzed propargylic substitution

Author keywords

Dioxanes; Morpholines; Platinum catalysis; Propargylic substitution; Sulfamates; Tetrahydropyrans

Indexed keywords

2 (4 HEX 1 YN 1 YL) 1,4 DIOXANE; 2 (4 OCTBUT 1 YN 1 YL) 1,4 DIOXANE; 2 (4 PHENYLBUT 1 YN 1 YL) 1,4 DIOXANE; 2 (OCT 1 YN 1 YL) 6 PHENYL 1,4 DIOXANE; 2 (PHENYLETHYL) 1,4 DIOXANE; 2 ETHYL 6 (HEX 1 YN 1 YL) 1,4 DIOXANE; 2 ETHYL 6 (OCT 1 YN 1 YL) 1,4 DIOXANE; 2 PHENYL 6 (PHENYLETHYL) 1,4 DIOXANE; 3 (4 PHENYLBUT 1 YN 1 YL) 4 TOSYLMORPHOLINE; 3 (HEX 1 YN 1 YL) 4 TOSYLMORPHOLINE; 3 (OCT 1 YN 1 YL) 4 TOSYLMORPHOLINE; 3 (PHENYLETHYNYL) 4 TOSYLMORPHOLINE; ALKYNE DERIVATIVE; DIOXANE; HETEROCYCLIC COMPOUND; MORPHOLINE; NUCLEOPHILE; PLATINUM; PROPARGYLIC ACETATE; SULFAMIC ACID; SULFUR DERIVATIVE; TERT BUTYL 2 (4 PHENYLBUT 1 YN 1 YL)MORPHOLINE 4 CARBOXYLATE; TERT BUTYL 2 (OCT 1 YN 1 YL)MORPHOLINE 4 CARBOXYLATE; TERT BUTYL 2 (PHENYLETHYL)MORPHOLINE 4 CARBOXYLATE; TERT BUTYL 2 ETHYL 6 (4 PHENYLBUT 1 YN 1 YL)MORPHOLINE 4 CARBOXYLATE; TERT BUTYL 2 ETHYL 6 (OCT 1 YN 1 YL)MORPHOLINE 4 CARBOXYLATE; TERT BUTYL 2 ISOPROPYL 6 (4 PHENYLBUT 1 YN 1 YL)MORPHOLINE 4 CARBOXYLATE; TERT BUTYL 2 PHENYL 6 (4 PHENYLBUT 1 YN 1 YL)MORPHOLINE 4 CARBOXYLATE; TERT BUTYL 2 PHENYL 6 (PHENYLETHYL)MORPHOLINE 4 CARBOXYLATE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

EID: 79958695955     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.03.115     Document Type: Article
Times cited : (13)

References (59)
  • 1
    • 70349784870 scopus 로고    scopus 로고
    • For selected reviews and examples see: (a)
    • For selected reviews and examples see: (a) Kumar, K.; Waldmann, H. Angew. Chem., Int. Ed. 2009, 48, 3224-3242;
    • (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 3224-3242
    • Kumar, K.1    Waldmann, H.2
  • 7
    • 33750320846 scopus 로고    scopus 로고
    • For a cycloisomerization strategy towards spiroketals, tetrahydrofuranyl, and tetrahydropyranyl acetals from our laboratory, see
    • (b) For a cycloisomerization strategy towards spiroketals, tetrahydrofuranyl, and tetrahydropyranyl acetals from our laboratory, see: Liu, B.; De Brabander, J. K. Org. Lett. 2006, 8, 4907-4910.
    • (2006) Org. Lett. , vol.8 , pp. 4907-4910
    • Liu, B.1    De Brabander, J.K.2
  • 8
    • 0032513707 scopus 로고    scopus 로고
    • In an important precedent, it was demonstrated that replacement of the tetrahydropyran B-ring of the bryostatins with a dioxane heterocycle not only significantly improved synthetic access, but also provided analogs with equal or superior biological activity, see
    • In an important precedent, it was demonstrated that replacement of the tetrahydropyran B-ring of the bryostatins with a dioxane heterocycle not only significantly improved synthetic access, but also provided analogs with equal or superior biological activity, see: Wender, P. A.; DeBrabander, J.; Harran, P. G.; Jimenez, J.-M.; Koehler, M. F. T.; Lippa, B.; Park, C.-M.; Shiozaki, M. J. Am. Chem. Soc. 1998, 120, 4534-4535.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 4534-4535
    • Wender, P.A.1    DeBrabander, J.2    Harran, P.G.3    Jimenez, J.-M.4    Koehler, M.F.T.5    Lippa, B.6    Park, C.-M.7    Shiozaki, M.8
  • 36
    • 79958710302 scopus 로고    scopus 로고
    • See the Supplementary data for details
    • See the Supplementary data for details.
  • 37
    • 84943002905 scopus 로고
    • For a detailed study on propargylic ester/allenyl ester epimerization, see
    • For a detailed study on propargylic ester/allenyl ester epimerization, see: Schlossarczyk, H.; Sieber, W.; Hesse, M.; Hansen, H.-J.; Scmid, H. Helv. Chim. Acta 1973, 56, 875-944.
    • (1973) Helv. Chim. Acta , vol.56 , pp. 875-944
    • Schlossarczyk, H.1    Sieber, W.2    Hesse, M.3    Hansen, H.-J.4    Scmid, H.5
  • 38
    • 79958736433 scopus 로고    scopus 로고
    • note
    • As for all propargylic substitutions reported herein, diastereomeric mixtures of starting materials (equimolar ratios) always converged to single diastereomeric products via a dynamic kinetic resolution. See Eq. 1 for a potential mechanism for epimerization at the propargylic center.
  • 40
    • 79958758675 scopus 로고    scopus 로고
    • N-Boc-protected amines were not effective substrates.
    • N-Boc-protected amines were not effective substrates.
  • 46
    • 79958738203 scopus 로고    scopus 로고
    • Chem. Abstr. 1998, 129, 337617.
    • (1998) Chem. Abstr. , vol.129 , pp. 337617
  • 48
    • 79958746685 scopus 로고
    • Chem. Abstr. 1978, 89, 80129.
    • (1978) Chem. Abstr. , vol.89 , pp. 80129


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.