메뉴 건너뛰기




Volumn 48, Issue 30, 2007, Pages 5185-5188

Surprising obtention of an enantiopure eight-membered cyclic ether from camphor

Author keywords

[No Author keywords available]

Indexed keywords

CAMPHOR; CYCLOBUTANE; EPOXIDE; ETHER DERIVATIVE; SPIRO COMPOUND; TRIFLUOROMETHANESULFONIC ACID;

EID: 34250814226     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.05.154     Document Type: Article
Times cited : (9)

References (61)
  • 9
    • 0000359232 scopus 로고
    • Scheuer P.J. (Ed), Academic Press, New York
    • Erikson K.L. In: Scheuer P.J. (Ed). Marine Natural Products Vol. 5 (1983), Academic Press, New York 131-257
    • (1983) Marine Natural Products , vol.5 , pp. 131-257
    • Erikson, K.L.1
  • 14
    • 33845662143 scopus 로고    scopus 로고
    • Some interesting reviews on the synthesis of medium-sized cyclic ethers are:. Kiyota H. (Ed), Springer, Berlin
    • Some interesting reviews on the synthesis of medium-sized cyclic ethers are:. Fujiwara K. In: Kiyota H. (Ed). Topics in Heterocyclic Chemistry Vol. 5 (2006), Springer, Berlin 97-148
    • (2006) Topics in Heterocyclic Chemistry , vol.5 , pp. 97-148
    • Fujiwara, K.1
  • 18
    • 0034246704 scopus 로고    scopus 로고
    • Yet L. Chem. Rev. 100 (2000) 2963
    • (2000) Chem. Rev. , vol.100 , pp. 2963
    • Yet, L.1
  • 40
    • 34250852077 scopus 로고    scopus 로고
    • note
    • For instance see Refs. 5c,f,j.
  • 42
    • 14044251506 scopus 로고    scopus 로고
    • Cyclobutanes are frequent key structural units in biologically important compounds: For instance see:
    • Cyclobutanes are frequent key structural units in biologically important compounds: For instance see:. Ortuño R.M., Moglioni G.Y., and Moltrasio G.Y. Curr. Org. Chem. 9 (2005) 237
    • (2005) Curr. Org. Chem. , vol.9 , pp. 237
    • Ortuño, R.M.1    Moglioni, G.Y.2    Moltrasio, G.Y.3
  • 45
    • 34250878774 scopus 로고    scopus 로고
    • note
    • 1J(C-H) coupling constants (132-134 Hz).
  • 46
    • 1242307349 scopus 로고    scopus 로고
    • The rate for the solvolysis of triflates via carbocationic processes can be improved using dimethyl sulfoxide as the solvent:
    • The rate for the solvolysis of triflates via carbocationic processes can be improved using dimethyl sulfoxide as the solvent:. Creary X., and Burtch E.A. J. Org. Chem. 69 (2004) 1227
    • (2004) J. Org. Chem. , vol.69 , pp. 1227
    • Creary, X.1    Burtch, E.A.2
  • 47
    • 34250813459 scopus 로고    scopus 로고
    • note
    • 13C HMQC and selective 1D NOESY NMR experiments. Key dinstintive dipolar interactions are related with the C3-exo methyl and the C2 and C7 epoxidic methylene groups.
  • 49
    • 0001693209 scopus 로고
    • Norbornane, bicyclo[2.1.1]heptane, cyclopentane, and cyclohexane are the common frameworks for products obtained by solvolysis of 1-norbornyl triflates. For instance, see:
    • Norbornane, bicyclo[2.1.1]heptane, cyclopentane, and cyclohexane are the common frameworks for products obtained by solvolysis of 1-norbornyl triflates. For instance, see:. Müller P., Mareda J., and Milin D. J. Phys. Org. Chem. 8 (1995) 507
    • (1995) J. Phys. Org. Chem. , vol.8 , pp. 507
    • Müller, P.1    Mareda, J.2    Milin, D.3
  • 50
    • 34250826874 scopus 로고
    • Olah G.A. (Ed), Wiley, New York Chapter 6
    • Müller P., and Mareda J. In: Olah G.A. (Ed). Cage Hydrocarbons (1991), Wiley, New York Chapter 6
    • (1991) Cage Hydrocarbons
    • Müller, P.1    Mareda, J.2
  • 54
    • 34250898370 scopus 로고    scopus 로고
    • note
    • Ionization has been also proposed as the first step for the solvolysis of related spiroepoxide 1-norbornyl triflates (i.e., Ref. 7).
  • 55
    • 1642300246 scopus 로고
    • To the best of our knowledge no precedents have been reported for the formation of the interesting bicyclo[2.2.0]hexane system by rearrangement of 1-norbornyl cations. In this sense, see an unfortunate attempt in:
    • To the best of our knowledge no precedents have been reported for the formation of the interesting bicyclo[2.2.0]hexane system by rearrangement of 1-norbornyl cations. In this sense, see an unfortunate attempt in:. Applequist D.E., and Klieman J.P. J. Org. Chem. 26 (1961) 2178
    • (1961) J. Org. Chem. , vol.26 , pp. 2178
    • Applequist, D.E.1    Klieman, J.P.2
  • 56
    • 34250823282 scopus 로고    scopus 로고
    • note
    • Several reports have revealed that eight-membered rings are better formed if conformational restrictions imposed by an existing ring or other functional groups are present in the precursor (e.g., see Ref. 4b and references cited therein).
  • 57
    • 34250865373 scopus 로고    scopus 로고
    • note
    • Suzuki et al. have taken advantage of 8-exo-tet hydroxy epoxide cyclizations for the total syntheses of several interesting natural eight-membered cyclic ethers. For instance see Ref. 5a and references cited therein.
  • 58
    • 34250833098 scopus 로고    scopus 로고
    • note
    • Acid catalysis is probably acting in the process. A synchronous 7-to-9 step cannot be discarded.
  • 59
    • 34250847423 scopus 로고    scopus 로고
    • note
    • +{radical dot}, 20), 181 (5), 165 (13), 150 (13), 137 (23), 123 (24), 109 (29), 107 (31), 95 (100), 81 (48), 67 (48), 55 (36).
  • 60
    • 34250800665 scopus 로고    scopus 로고
    • note
    • C2-C3 rearrangement is the common observed process for related spiroepoxide 1-norbornyl triflates (Ref. 7).
  • 61
    • 34250875477 scopus 로고    scopus 로고
    • note
    • Note the undetected 6-exo-tet hydroxy-epoxide cyclization of 10, under the used reaction conditions, probably due to the unfavorable, and conformationally-restricted, disposition of both reacting groups.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.