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Volumn 52, Issue 37, 2013, Pages 9751-9754

Regioselective Wacker oxidation of internal alkenes: Rapid access to functionalized ketones facilitated by cross-metathesis

Author keywords

ketones; metathesis; oxidation; palladium; regioselectivity

Indexed keywords

BENZOQUINONES; CROSS METATHESIS; DIRECTING GROUPS; FUNCTIONALIZED; METATHESIS; REGIO-SELECTIVE; REGIOSELECTIVE OXIDATION; WACKER OXIDATION;

EID: 84883513574     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201303587     Document Type: Article
Times cited : (50)

References (53)
  • 19
    • 84864976010 scopus 로고    scopus 로고
    • For an interesting example of catalyst-controlled regioselectivity in Wacker-type oxidation of terminal allylic phthalimide, see:, B. W. Michel, J. R. McCombs, A. Winkler, M. S. Sigman, Angew. Chem. 2010, 122, 7470
    • (2010) Angew. Chem. , vol.122 , pp. 7470
    • Michel, B.W.1    McCombs, J.R.2    Winkler, A.3    Sigman, M.S.4
  • 23
    • 79960382300 scopus 로고    scopus 로고
    • Unsuccessful reactions using coordinating groups (yield <50 %)
    • S. B. Narute, N. C. Kiran, C. V. Ramana, Org. Biomol. Chem. 2011, 9, 5469. Unsuccessful reactions using coordinating groups (yield <50 %)
    • (2011) Org. Biomol. Chem. , vol.9 , pp. 5469
    • Narute, S.B.1    Kiran, N.C.2    Ramana, C.V.3
  • 32
    • 30744475459 scopus 로고    scopus 로고
    • J. A. Wright, M. J. Gaunt, J. B. Spencer, Chem. Eur. J. 2006, 12, 949. We recently described two anti-Markovnikov palladium-catalyzed reactions using benzoquinone
    • (2006) Chem. Eur. J. , vol.12 , pp. 949
    • Wright, J.A.1    Gaunt, M.J.2    Spencer, J.B.3
  • 39
    • 77955183860 scopus 로고    scopus 로고
    • This result emphasizes the need for further mechanistic study in Wacker oxidation chemistry. See:, J. A. Keith, P. M. Henry, Angew. Chem. 2009, 121, 9200
    • (2009) Angew. Chem. , vol.121 , pp. 9200
    • Keith, J.A.1    Henry, P.M.2
  • 47
    • 84871978691 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2013, 52, 310; For alternative Z-selective cross-metathesis based on Mo, see
    • (2013) Angew. Chem. Int. Ed. , vol.52 , pp. 310
  • 51
    • 55449097589 scopus 로고    scopus 로고
    • For a critical discussion of the application of catalysis to renewable resources, see:, M. Beller, Eur. J. Lipid Sci. Technol. 2008, 110, 789.
    • (2008) Eur. J. Lipid Sci. Technol. , vol.110 , pp. 789
    • Beller, M.1
  • 53
    • 0001736452 scopus 로고
    • Chelation-control has been suggested in the Wacker oxidation of terminal alkenes. See:, J. Tsuji, H. Nagashima, K. Hori, Tetrahedron Lett. 1982, 23, 2679.
    • (1982) Tetrahedron Lett. , vol.23 , pp. 2679
    • Tsuji, J.1    Nagashima, H.2    Hori, K.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.