Samarium(II) iodide-promoted hydroxyalkylations of indole 3-carbonyls. An expedient approach to pyrrolidino[1,2-a]indoles and furo[3,4-b]indoles

Journal of the Chemical Society, Chemical Communications

Volumn , Issue 16, 1993, Pages 1277-1278

  Shiue, Jiann Shyng ^a   Fang, Jim Min ^a  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542377045     PISSN: 00224936     EISSN: None     Source Type: Journal    
DOI: 10.1039/C39930001277     Document Type: Article

References (11)

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2. G.A. Molander, Chem. Rev., 92, 29.
3. G.A. Molander, Comprehensive Organic Synthesis, 1, 251, 282B. M. Trost, I. Fleming, Pergamon, Oxford.
4. J.-S. Shiue, C.-C. Lin and J.-M. Fang, Tetrahedron Lett., 34, 335.
5. J. Inanaga, Rev. Heteroat. Chem., 3, 75, The use of HMPA has been found to facilitate the reactions involving SmI2 such as reduction of halides, deoxygenation of sulfones, Barbier-type reactions, ketone–olefin couplings and in other radical cyclizations of carbon–carbon unsaturated systems. See ref. 2 and, references cited therein.
6. R.W. Franck, Progress in the Chemistry of Organic Natural Products, 1, W. Herz, H. Grisebach, G. W. Kirby, Springer, Vienna.
7. W. Verboom and D.N. Reinhoudt, Recl. Trav. Chim. Pays-Bas, 105, 199.
8. U. Pindur and H. Erfanian-Abdoust, Chem. Rev., 89, 1681.
9. G.W. Gribble, D.J. Keavy, D.A. Davis, M.G. Saulnier, B. Pelcman, T.C. Barden, M.P. Sibi, E.R. Olson and J.J. BelBruno, J. Org. Chem., 57, 5878.
10. C.-C. Yang, H.-T. Chang and J.-M. Fang, J. Org. Chem., 58, 3100, Compound 4 existed as a single isomer as revealed by its 1H and 13C NMR spectra, however, the stereochemistry was not determined.
11. P. Girard, J.L. Namy and H.B. Kagan, J. Am. Chem. Soc., 102, 2693.