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Volumn 12, Issue 2, 2010, Pages 260-263

Enantioselective palladium(II)-catalyzed formal [3,3]-sigmatropic rearrangement of 2-allyloxypyridines and related heterocycles

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; HETEROCYCLIC COMPOUND; ORGANOMETALLIC COMPOUND; PALLADIUM; PYRIDINE DERIVATIVE;

EID: 74949098369     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9025759     Document Type: Article
Times cited : (70)

References (45)
  • 18
    • 37049103557 scopus 로고
    • Similar problems and low yields have been, reported in the rearrangements of other 2-allyloxy N-heterocycles, such as tetrachloropyridines, quinolines, isoquinolines, benzoxazoles, benzthiazoles, and tetrazoles. See: (a) Iddon, B.; Hans, S.; Taylor, J. A. J. Chem. Soc., Perkin Trans. 1 1979, 2756-2761.
    • (1979) J. Chem. Soc., Perkin Trans. , vol.1 , pp. 2756-2761
    • Iddon, B.1    Hans, S.2    Taylor, J.A.3
  • 23
    • 0141742434 scopus 로고    scopus 로고
    • Pd(O)-catalyzed rearrangement of E-crotyloxypyridine leads to a mixture of both, formal [1,3]- and [3,3]-sigmatropic rearranged products, whereas Pd(II) leads to clean [3,3]-rearrangement: Itami, K.; Yamazaki, D.; Yoshida, J. Org. Lett. 2003, 5, 2161-2164.
    • (2003) Org. Lett. , vol.5 , pp. 2161-2164
    • Itami, K.1    Yamazaki, D.2    Yoshida, J.3
  • 26
    • 33646064214 scopus 로고    scopus 로고
    • The allylie trichloroacetimidate rearrangement
    • Overman, L. E., Ed.; Wiley: Hoboken, NJ
    • For a general overview of the Overman rearrangement, see: Overman, L. E.; Carpenter, N. E. The Allylie Trichloroacetimidate Rearrangement. In Organic Reactions; Overman, L. E., Ed.; Wiley: Hoboken, NJ, 2005; Vol.66, pp 1-107.
    • (2005) Organic Reactions , vol.66 , pp. 1-107
    • Overman, L.E.1    Carpenter, N.E.2
  • 42
    • 74949108836 scopus 로고    scopus 로고
    • See the Supporting Information for details
    • See the Supporting Information for details.
  • 43
    • 74949087243 scopus 로고    scopus 로고
    • Substrates 11a - e were prepared in a similar fashion to substrate 8 with conventional heating at 50 °C over 40 h instead of microwave heating
    • Substrates 11a - e were prepared in a similar fashion to substrate 8 with conventional heating at 50 °C over 40 h instead of microwave heating.
  • 44
    • 74949091439 scopus 로고    scopus 로고
    • 2-Allyloxypyrimidines have been reported to not undergo thermal rearrangement at 200 °C. See ref 8d
    • 2-Allyloxypyrimidines have been reported to not undergo thermal rearrangement at 200 °C. See ref 8d.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.