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Volumn 8, Issue 12, 2006, Pages 2627-2630

Facile regio- and stereoselective carbon-carbon coupling of phenol derivatives with aryl aziridines

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EID: 33745540080     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol060822m     Document Type: Article
Times cited : (33)

References (33)
  • 1
    • 1542375289 scopus 로고    scopus 로고
    • For a recent review, see: Hu, X. E. Tetrahedron 2004, 60, 2701.
    • (2004) Tetrahedron , vol.60 , pp. 2701
    • Hu, X.E.1
  • 16
    • 33745516068 scopus 로고    scopus 로고
    • note
    • 2 (40 mL) and washed with brine. Evaporation of the dried organic solution afforded a crude reaction mixture that was purified by silica gel chromatography to give the corresponding pure products.
  • 18
    • 16244373597 scopus 로고
    • Moreover, it should be considered that the electron density on phenolic oxygen is low because of pπ-pπ back-bonding with the boron atom. For a study of the Lewis acidity of the boron atom in triarylborates, see: (a) Fenwick, J. T. F.; Wilson, J. W. Inorg. Chem. 1975, 14, 1602.
    • (1975) Inorg. Chem. , vol.14 , pp. 1602
    • Fenwick, J.T.F.1    Wilson, J.W.2
  • 20
    • 33745533500 scopus 로고    scopus 로고
    • note
    • However, with some disubstituted aziridines and aryl borates, lower yields and stereoselectivities were obtained. For other examples of the use of disubstituted aziridines, see Supporting Information.
  • 21
    • 0027180141 scopus 로고
    • For a review, see: (a) Ritter, K. Synthesis 1993, 735.
    • (1993) Synthesis , pp. 735
    • Ritter, K.1
  • 24
    • 3142732882 scopus 로고    scopus 로고
    • and pertinent references therein
    • For a recent highly enantioselective synthesis of chiral 3-substituted indolines by catalytic asymmetric hydrogenation of indoles, see: Kuwano, R.; Kaneda, K.; Ito, T.; Sato, K.; Kurokawa, T.; Ito, Y. Org. Lett. 2004, 6, 2213 and pertinent references therein.
    • (2004) Org. Lett. , vol.6 , pp. 2213
    • Kuwano, R.1    Kaneda, K.2    Ito, T.3    Sato, K.4    Kurokawa, T.5    Ito, Y.6
  • 27
    • 16244411305 scopus 로고    scopus 로고
    • and references therein
    • For a recent mechanistic study of the Goldberg amidation reactions, see: Strieter, E. R.; Blackmond, D. G.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4120 and references therein.
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 4120
    • Strieter, E.R.1    Blackmond, D.G.2    Buchwald, S.L.3
  • 30
    • 0035912362 scopus 로고    scopus 로고
    • 16 proved to be unsuccessful for the intramolecular ring closure of triflates 5
    • 16 proved to be unsuccessful for the intramolecular ring closure of triflates 5.
    • (2001) Org. Lett. , vol.3 , pp. 1141
    • Coleman, R.S.1    Chen, W.2
  • 32
    • 33744870975 scopus 로고    scopus 로고
    • It should be noted that trans 2,3-substituted indolines are difficult to obtain by other routes and cannot be obtained by catalytic hydrogenation of the corresponding 2,3-substituted indoles. For an efficient synthesis of 2,3-disubstituted indoles, see: (a) Larock, R. C.; Yum, E. K.; Refvik, M. D. J. Org. Chem. 1998, 63, 7652.
    • (1998) J. Org. Chem. , vol.63 , pp. 7652
    • Larock, R.C.1    Yum, E.K.2    Refvik, M.D.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.