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Volumn 12, Issue 10, 2010, Pages 2198-2201

Combined directed ortho metalation-halogen dance (HD) synthetic strategies. HD-anionic ortho fries rearrangement and double HD sequences

Author keywords

[No Author keywords available]

Indexed keywords

CARBAMIC ACID DERIVATIVE;

EID: 77952363131     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol100493v     Document Type: Article
Times cited : (51)

References (58)
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    • Transition metals in the synthesis of heterocycles
    • Transition metals in the synthesis of heterocycles
  • 3
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    • Tandem/cascade reactions in total synthesis:
    • Tandem/cascade reactions in total synthesis:
  • 5
    • 77952373049 scopus 로고    scopus 로고
    • Domino reactions
    • Domino reactions
  • 13
    • 77952402382 scopus 로고    scopus 로고
    • Discovery
    • Discovery
  • 23
    • 77952394165 scopus 로고    scopus 로고
    • For HD on picolinamides, see
    • For HD on picolinamides, see
  • 25
    • 77952332205 scopus 로고    scopus 로고
    • Caerulomycin
    • Caerulomycin
  • 30
    • 77952387694 scopus 로고    scopus 로고
    • For applications, see
    • For applications, see
  • 33
    • 0000385213 scopus 로고
    • Anionic Fries rearrangement
    • Anionic Fries rearrangement: Sibi, M. P.; Snieckus, V. J. Org. Chem. 1983, 48, 1935
    • (1983) J. Org. Chem. , vol.48 , pp. 1935
    • Sibi, M.P.1    Snieckus, V.2
  • 36
    • 77952355740 scopus 로고    scopus 로고
    • For recent thorough mechanistic studies, see
    • For recent thorough mechanistic studies, see
  • 40
    • 77952357667 scopus 로고
    • First observed in the studies of, University of Waterloo, ON, Canada
    • First observed in the studies of Tsukazaki, M. Ph.D. Thesis, University of Waterloo, ON, Canada, 1995.
    • (1995) Ph.D. Thesis
    • Tsukazaki, M.1
  • 41
    • 77952390524 scopus 로고    scopus 로고
    • The significance of N -coordination for driving new regioselectivity is nicely demonstrated by the work of Fort; see
    • The significance of N -coordination for driving new regioselectivity is nicely demonstrated by the work of Fort; see
  • 43
    • 0003397781 scopus 로고    scopus 로고
    • de Meijere, A.; Diederich, F., Eds.; Wiley-VCH: Weinheim
    • Metal-Catalyzed Cross-Coupling Reactions II; de Meijere, A.; Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004.
    • (2004) Metal-Catalyzed Cross-Coupling Reactions II
  • 44
    • 77952399221 scopus 로고    scopus 로고
    • note
    • Compatibility of LDA and TMSCl first established by Martin and Quéguiner
  • 47
    • 77952391992 scopus 로고    scopus 로고
    • note
    • A similar one-pot D o M-HD reaction of pyrimidine with an excess of base was described by Quéguiner
  • 49
    • 77952413026 scopus 로고    scopus 로고
    • Noteworthy are the extensive contributions of Schlosser (review)
    • Noteworthy are the extensive contributions of Schlosser (review)
  • 51
    • 77952336697 scopus 로고    scopus 로고
    • For a single report concerning a combined HD-A o F of a iodo quinoline O -carbamate, see
    • For a single report concerning a combined HD-A o F of a iodo quinoline O -carbamate, see
  • 54
    • 77952354771 scopus 로고    scopus 로고
    • note
    • Typically, O -carbamates are metalated with s -BuLi/TMEDA under standard conditions and the resulting lithiated species are allowed to warm to room temperature (10-12 h); see ref 7b. In the present studies, LDA is used as the base to prevent lithium-halogen exchange reactions.
  • 56
    • 77952336202 scopus 로고    scopus 로고
    • Katritzky, A. R.; Pozharskii, A. F., Eds.; Pergamon: Oxford
    • Handbook of Heterocyclic Chemistry; Katritzky, A. R.; Pozharskii, A. F., Eds.; Pergamon: Oxford, 2000; pp 545 - 546.
    • (2000) Handbook of Heterocyclic Chemistry , pp. 545-546


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.