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Volumn 8, Issue 18, 2006, Pages 3919-3922

[3+2] versus [4+2] cycloadditions of quinone monoimide with azadienes: A Lewis acid-free access to 5-amino-2,3-dihydrobenzofuranes

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EID: 33748949232     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061184a     Document Type: Article
Times cited : (25)

References (33)
  • 8
    • 0032537701 scopus 로고    scopus 로고
    • This strategy has been exploited in the quinone series for the preparation of various heterocycles: (a) Kitahara, Y.; Tamura, F.; Nishimura, M.; Kubo, A. Tetrahedron 1998, 54, 8421.
    • (1998) Tetrahedron , vol.54 , pp. 8421
    • Kitahara, Y.1    Tamura, F.2    Nishimura, M.3    Kubo, A.4
  • 12
    • 0001061931 scopus 로고
    • 3) to proceed in a 38% yield (20 h reaction time, 23 °C): Echavarren, A. M. J. Org. Chem. 1990, 55, 4255.
    • (1990) J. Org. Chem. , vol.55 , pp. 4255
    • Echavarren, A.M.1
  • 13
    • 33748919167 scopus 로고    scopus 로고
    • note
    • For an optimized synthesis of compound 5 involving its selective precipitation, see Supporting Information.
  • 14
    • 33748934103 scopus 로고    scopus 로고
    • note
    • 3 generally contains acid traces which behave as a catalyst for the transformation of the keto compound 5 into the phenol 7.
  • 15
    • 33748920249 scopus 로고    scopus 로고
    • note
    • 1H NMR after a 22 h stay at 25 °C.
  • 16
    • 33748925984 scopus 로고    scopus 로고
    • note
    • 2 nitrogen is 2.21 Å (measured on the X-ray crystal structure).
  • 31
    • 33748922493 scopus 로고    scopus 로고
    • note
    • The use of a 2-fold excess of 1a led to a more complex reaction mixture: this could be explained by the oxidizing properties of the quinoid compound 1a.
  • 32
    • 33748925279 scopus 로고    scopus 로고
    • note
    • 2 = H) led to a complex mixture with only traces of the corresponding DHBF.
  • 33
    • 32644439884 scopus 로고    scopus 로고
    • For a review on the construction of enantioenriched quaternary stereocenters, see: Trost, B. M.; Jiang, C. Synthesis 2006, 369.
    • (2006) Synthesis , pp. 369
    • Trost, B.M.1    Jiang, C.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.