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Volumn 13, Issue 24, 2011, Pages 6588-6591

Intramolecular [2 + 2] Cycloaddition reactions of alkynyl ether derived ketenes. a convenient synthesis of donor-acceptor cyclobutanes

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ALKYNE; CYCLOBUTANE DERIVATIVE; ETHER DERIVATIVE;

EID: 84055178126     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol202989c     Document Type: Article
Times cited : (20)

References (35)
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    • (b) Fu, N.-Y.; Chan, S.-H. In The Chemistry of Cyclobutanes; Rappoport, Z., Liebman, J. F., Eds.; J. Wiley & Sons: Chichester,NY, 2005; p 357.
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    • Fu, N.-Y.1    Chan, S.-H.2
  • 3
    • 0001362730 scopus 로고
    • (c) For an elegant application of cylobutanone ring expansion in natural product synthesis, see: Corey, E. J.; Desai,M. C.; Engler, T. A. J. Am. Chem. Soc. 1985, 107, 4339.
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 4339
    • Corey, E.J.1    Desai, M.C.2    Engler, T.A.3
  • 4
    • 34848844912 scopus 로고    scopus 로고
    • Rappoport, Z., Liebman, J. F., Eds.; J. Wiley & Sons: Chichester, NY
    • (a) Lee-Ruff, E. In The Chemistry of Cyclobutanes; Rappoport, Z., Liebman, J. F., Eds.; J. Wiley & Sons: Chichester, NY, 2005; p 281.
    • (2005) The Chemistry of Cyclobutanes , pp. 281
    • Lee-Ruff, E.1
  • 5
    • 0002813579 scopus 로고
    • Marchand A. P.; Lehr R. E. Eds.; Academic Press: New York
    • (b) Ghosez, L.; O'Donnell, M. J. Pericyclic Reactions; Marchand, A. P., Lehr, R. E., Eds.; Academic Press: New York, 1977; Vol. II, p 79.
    • (1977) Pericyclic Reactions , vol.2 , pp. 79
    • Ghosez, L.1    O'donnell, M.J.2
  • 13
    • 29244475030 scopus 로고
    • Viehe, H. G., Ed.; Marcel Dekker: New York
    • For reviews of the chemistry of ynol ethers and the methods for the synthesis of ynol ethers, see: (a) Brandsma, L.; Bos, H. J.; Arens, J. F. In The Chemistry of Acetylenes; Viehe, H. G., Ed.; Marcel Dekker: New York, 1969; pp 751-860.
    • (1969) The Chemistry of Acetylenes , pp. 751-860
    • Brandsma, L.1    Bos, H.J.2    Arens, J.F.3
  • 30
    • 67650292726 scopus 로고    scopus 로고
    • Compound 3i was prepared in four steps from commercially available 2-bromobenzaldehyde diethyl acetal by copper-catalyzed allylation of the corresponding Grignard reagent (Mg, THF; cat. CuI, methallyl mesylate), hydrolysis of the diethyl acetal (acetone, cat. TsOH), addition of tert-butoxyethynyllithium (THF, -78 °C), and protection of the benzylic alcohol as its ethoxymethyl acetal (EtOCH2Cl, DIEA, 2 h, rt). See: Lin, S.; Song, C.-X.; Cai, G.-X.;Wang,W.-H.; Shi, Z.-J. J. Am. Chem. Soc. 2008, 130, 12901.
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 12901
    • Lin, S.1    Song, C.-X.2    Cai, G.-X.3    Wang, W.-H.4    Shi, Z.-J.5
  • 32
    • 77956652752 scopus 로고    scopus 로고
    • The alkylating agent 3-bromo-2-(ethoxymethoxy)prop-1-ene used for the preparation of 3p-r was synthesized from1,3-dibromo-2-propanol. See: Dhanjee, H.; Minehan, T. G. Tetrahedron Lett. 2010, 51, 5609.
    • (2010) Tetrahedron Lett. , vol.51 , pp. 5609
    • Dhanjee, H.1    Minehan, T.G.2
  • 33
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    • Matsuo has demonstrated Lewis acid promoted formal [4 + 2] cycloaddition reactions between 3-alkoxycyclobutanones and aldehydes, ketones, allylsilanes, and silylenol ethers: (a) Matsuo, J.-i.; Sasaki, S.; Hoshikawa, T.; Ishibashi, H. Org. Lett. 2009, 11, 3822.
    • (2009) Org. Lett. , vol.11 , pp. 3822
    • Matsuo, J.-I.1    Sasaki, S.2    Hoshikawa, T.3    Ishibashi, H.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.