Iodine transfer cyclization mediated by DIBAL-H/THF

Chemical Communications

Volumn , Issue 23, 1999, Pages 2375-2376

  Chakraborty, Arindam ^a   Marek, Ilan ^a  

^a TECHNION ISRAEL INSTITUTE OF TECHNOLOGY   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; IODINE; RADICAL; TETRAHYDROFURAN DERIVATIVE;

ARTICLE; CHEMICAL BOND; CYCLIZATION; ISOMERISM; REACTION ANALYSIS; SYNTHESIS;

EID: 0033534067     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a906952f     Document Type: Article

References (34)

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24. Radical cyclizations mediated by organometallic derivatives were described in the literature but without any iodine transfer. H. Stadtmuller, A. Vaupel, C. E. Tucker, T. Studemann and P. Knochel, Chem. Eur. J., 1996, 2, 1204; J. Tang, H. Shinokubo and K. Oshima, Synlett, 1998, 1075; Y. Hayashi, H. Shinokubo and K. Oshima, Tetrahedron Lett., 1998, 39, 63; F. Villar and P. Renaud, Tetrahedron Lett., 1998, 39, 8655.
25. Radical cyclizations mediated by organometallic derivatives were described in the literature but without any iodine transfer. H. Stadtmuller, A. Vaupel, C. E. Tucker, T. Studemann and P. Knochel, Chem. Eur. J., 1996, 2, 1204; J. Tang, H. Shinokubo and K. Oshima, Synlett, 1998, 1075; Y. Hayashi, H. Shinokubo and K. Oshima, Tetrahedron Lett., 1998, 39, 63; F. Villar and P. Renaud, Tetrahedron Lett., 1998, 39, 8655.
26. Radical cyclizations mediated by organometallic derivatives were described in the literature but without any iodine transfer. H. Stadtmuller, A. Vaupel, C. E. Tucker, T. Studemann and P. Knochel, Chem. Eur. J., 1996, 2, 1204; J. Tang, H. Shinokubo and K. Oshima, Synlett, 1998, 1075; Y. Hayashi, H. Shinokubo and K. Oshima, Tetrahedron Lett., 1998, 39, 63; F. Villar and P. Renaud, Tetrahedron Lett., 1998, 39, 8655.
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29. Moreover, the intramolecular addition of an organometallic across a triple bond is known to be a syn process. See ref. 5.
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33. 4) and then the solvent was evaporated to provide the crude product. After purification by chromatography on silica gel (10% EtOAc in hexanes), 421 mg (90%) of the title compound was obtained
34. All our attempts to form the six-membered ring as well as to promote the isomerization across a double bond failed.