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Volumn 73, Issue 8, 2008, Pages 3218-3227

Diastereoselective ru-catalyzed cross-metathesis-dihydroxylation sequence. An efficient approach toward enantiomerically enriched syn-diols

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST ACTIVITY; ENANTIOMERS; STEREOSELECTIVITY;

EID: 42149187130     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800145x     Document Type: Article
Times cited : (110)

References (52)
  • 17
    • 0141521468 scopus 로고    scopus 로고
    • Ru-catalyzed dihydroxylation: (a) Plietker, B.; Niggemann, M. Org. Lett. 2003, 5, 3353.
    • Ru-catalyzed dihydroxylation: (a) Plietker, B.; Niggemann, M. Org. Lett. 2003, 5, 3353.
  • 20
    • 0042285952 scopus 로고    scopus 로고
    • (d) Plietker, B
    • RuO4-catalyzed ketohydroxylation
    • 4-catalyzed ketohydroxylation. (d) Plietker, B. J. Org. Chem. 2003, 68, 7123.
    • (2003) J. Org. Chem , vol.68 , pp. 7123
  • 23
    • 42149143405 scopus 로고    scopus 로고
    • While this work was in progress, two independent reports on the sequential cross-metathesis-dihydroxylation starting from methyl acrylate and various olefins appeared. However, the syn-diols were obtained as a racemate, a Beligny, S, Eibauer, S, Maechling, S, Blechert, S. Angew. Chem. 2006, 119, 1933;
    • While this work was in progress, two independent reports on the sequential cross-metathesis-dihydroxylation starting from methyl acrylate and various olefins appeared. However, the syn-diols were obtained as a racemate. (a) Beligny, S.; Eibauer, S.; Maechling, S.; Blechert, S. Angew. Chem. 2006, 119, 1933;
  • 24
    • 33646763502 scopus 로고    scopus 로고
    • Angew. Chem., Int. Ed. 2006, 45, 1900-1903.
    • (2006) Angew. Chem., Int. Ed , vol.45 , pp. 1900-1903
  • 34
    • 33749017670 scopus 로고    scopus 로고
    • Angew. Chem., Int. Ed. 2006, 45, 6218-6221.
    • (2006) Angew. Chem., Int. Ed , vol.45 , pp. 6218-6221
  • 36
    • 33645501568 scopus 로고    scopus 로고
    • This method was successfully applied in synthesis; for a prominent example see: Tiwari, P, Misra, A. K. J. Org. Chem. 2006, 71, 2911
    • This method was successfully applied in synthesis; for a prominent example see: Tiwari, P.; Misra, A. K. J. Org. Chem. 2006, 71, 2911.
  • 40
    • 42149184612 scopus 로고    scopus 로고
    • The β-substituent was shown to significantly decrease the stereo-selectivity in auxiliary-induced RuO4-catalyzed dihydroxylations and was therefore chosen as a suitable model compound. See ref 11
    • 4-catalyzed dihydroxylations and was therefore chosen as a suitable model compound. See ref 11.
  • 45
    • 42149128737 scopus 로고    scopus 로고
    • A figure of the apparatus is shown in the Supporting Information
    • A figure of the apparatus is shown in the Supporting Information.
  • 50
    • 42149182871 scopus 로고    scopus 로고
    • The observed stability of Grela's catalyst underlines its reported extraordinary stability toward oxidation. See ref 18
    • The observed stability of Grela's catalyst underlines its reported extraordinary stability toward oxidation. See ref 18.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.