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Volumn 55, Issue 29, 1999, Pages 8953-8966

Intramolecular conjugate addition reactions of amines and carbamates to 2,5-cyclohexadien-1-ones: Stereoselective synthesis of perhydroindoles

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; CARBAMIC ACID DERIVATIVE; INDOLE DERIVATIVE; KETONE;

EID: 0033575412     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00455-X     Document Type: Conference Paper
Times cited : (30)

References (32)
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    • (1992) Tetrahedron Lett. , vol.33 , pp. 5477
    • Wipf, P.1    Kim, Y.2
  • 6
    • 0032125867 scopus 로고    scopus 로고
    • For the first total synthesis of manzamine A see: Winkler, J. D.; Axten, M. M. J. Am. Chem. Soc. 1998, 120, 6425. For a relevant review see: Matzanke, N.; Gregg, R. J.; Weinreb, S. M. Org Prep. Proc. Int. 1998, 30, 1.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 6425
    • Winkler, J.D.1    Axten, M.M.2
  • 7
    • 0002531060 scopus 로고    scopus 로고
    • For the first total synthesis of manzamine A see: Winkler, J. D.; Axten, M. M. J. Am. Chem. Soc. 1998, 120, 6425. For a relevant review see: Matzanke, N.; Gregg, R. J.; Weinreb, S. M. Org Prep. Proc. Int. 1998, 30, 1.
    • (1998) Org Prep. Proc. Int. , vol.30 , pp. 1
    • Matzanke, N.1    Gregg, R.J.2    Weinreb, S.M.3
  • 8
    • 0013590480 scopus 로고    scopus 로고
    • note
    • See reference 4 for a more convergent approach to 4 that ran into complications.
  • 10
    • 0001726652 scopus 로고
    • Ganem, B.; Small, V. R. Jr. J. Org. Chem. 1974, 39, 3728. Alexakis, A.; Gardette, M.; Colin, S. Tetrahedron Lett. 1988, 29, 2951.
    • (1974) J. Org. Chem. , vol.39 , pp. 3728
    • Ganem, B.1    Small V.R., Jr.2
  • 16
    • 0042420514 scopus 로고
    • Brown, H. C.; Brown, C. A. J. Am. Chem. Soc. 1963, 85, 1005. Millar, J. G.; Oehlschlager, A. C. J. Org. Chem. 1984, 49, 2332.
    • (1963) J. Am. Chem. Soc. , vol.85 , pp. 1005
    • Brown, H.C.1    Brown, C.A.2
  • 21
    • 0003161893 scopus 로고
    • Details appear in the PhD Thesis of Gilles Chambournier, The Ohio State University, 1998
    • 3-MeOH. Cyclization of I using CsF and epimerization studies with II were not performed. The synthesis of I from a known ester [Garner, P.; Park, J. M. Organic Syntheses 1992, 70, 18] is outlined near the top of the next page. Details appear in the PhD Thesis of Gilles Chambournier, The Ohio State University, 1998.
    • (1992) Organic Syntheses , vol.70 , pp. 18
    • Garner, P.1    Park, J.M.2
  • 22
    • 0013597998 scopus 로고    scopus 로고
    • note
    • -1 energy difference between 28a (lower) and 2-epi-28a.
  • 23
    • 0013620908 scopus 로고    scopus 로고
    • note
    • 2-hybridized orbital on the carbamate nitrogen (either in the anion or an imidate tautomer). This requires a different analysis of the problem that does not lead us to an obvious explanation for our experimental observations. This problem does seem to be a good candidate for computational analysis and such studies are planned. (formula presented)
  • 24
    • 0013596644 scopus 로고    scopus 로고
    • note
    • 2H, PhH, 77%
  • 27
    • 0013565645 scopus 로고    scopus 로고
    • note
    • Under basic conditions the malonate group in 38 underwent cyclization prior to the carbamate to provide a mixture of diastereomeric products. Thus, the use of acid-first and base-second is important to the timing of the two conjugate addition reactions.
  • 28
    • 0013565789 scopus 로고    scopus 로고
    • note
    • 8a-diastereomer to 28b. These results suggest that the stereochemical course of the transformation shown Scheme 2 (38→28b) is governed by thermodynamics.
  • 29
    • 0013619851 scopus 로고    scopus 로고
    • note
    • X-ray crystallography was performed by Dr. Judith C. Gallucci at The Ohio State University.
  • 31
    • 0013565646 scopus 로고    scopus 로고
    • note
    • 13C NMR were taken at 50-125 MHz in the indicated solvent and are reported as follows: chemical shift (multiplicity determined by DEPT). Chromatography was performed using either gravity or flash chromatography techniques as required. Solvents and reagents were dried and purified prior to use when deemed necessary using standard procedures. Reactions requiring an inert atmosphere were run under a blanket of argon.
  • 32
    • 0000762847 scopus 로고
    • This reagent was prepared by reaction of isobutylene with -hexyn-1-ol in hexanes in the presence of Amberlyst DV265 (Alexakis, A.; Gardette, M.; Colin, S. Tetrahedron Lett. 1988, 29, 2951).
    • (1988) Tetrahedron Lett. , vol.29 , pp. 2951
    • Alexakis, A.1    Gardette, M.2    Colin, S.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.