Stereoselective intramolecular O-H insertion of rhodium carbenoid controlled by the 2,4-pentanediol tether

Chemistry Letters

Volumn 34, Issue 10, 2005, Pages 1328-1329

  Chun, Young Im ^a   Okuyama, Tadashi ^a   Sugimura, Takashi ^a  

^a UNIVERSITY OF HYOGO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 29344441761     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2005.1328     Document Type: Article

References (15)

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4. M. P. Doyle and M. Yan, Tetrahedron Lett., 43, 5929 (2002).
5. T. Sugimura, in "Recent Research Developments in Organic Chemistry," ed. by S. G. Pandalai, Transworld Research Network, Trivandrum (1998), Vol. 2, pp 47-53;
6. T. Sugimura, Eur. J. Org. Chem., 2004, 1185.
7. T. Sugimura, S. Nagano, and A. Tai, Tetrahedron Lett., 38, 3547 (1997).
8. For intramolecular O-H insertion reactions, see: M. P. Moyer, P. L. Feldman, and H. Rapoport, J. Org. Chem., 50, 5223 (1985);
9. J. C. Heslin, C. J. Moody, A. M. Z. Slawin, and D. J. Williams, Tetrahedron Lett., 27, 1403 (1986);
10. J. C. Heslin and C. J. Moody, J. Chem. Soc., Perkin Trans. 1, 1988, 1417;
11. F. Sarabia-Garcia, F. J. Lopez-Herrera, and M. S. Pino-Gonzalez, Tetrahedron Lett., 35, 6709 (1994).
12. A common precursor for 3-5 was prepared in a stereochemically pure form by the Mitsunobu reaction of (R,R)-2,4-pentanediol and 2-t- butyldimethylsilyloxyphenol in 71% yield. Desilylation was achieved in a quantitative yield before or after the manipulation at the remaining hydroxy group to introduce the diazo esters. The substrate 9 was prepared through an additional Mitsunobu reaction with benzoic acid. 10 and 11 were prepared with 3-hydroxybutyl benzoate and 1,3-butanediol, respectively, in a similar way.
13. The conformation of the initial adduct was illustrated based on the results with the related PD-tethered reactions. See: T. Sugimura, K. Hagiya, Y. Sato, T. Tei, A. Tai, and T. Okuyama, Org. Lett., 3, 37 (2001).
14. w) = 0.070(0.066) for 2004 reflections with I > 2.0σ(I). Crystallographic data reported in this manuscript have been deposited with Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 281652 & 281653. Copies of the data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge, CB2 1EZ, UK; fax: +44 1223 336033; or deposit@ccdc.cam.ac.uk).
15. C. D. Lu, H. Liu, Z. Y. Chen, W. H. Hu, and A. Q. Mi, Org. Lett., 7, 83 (2005), and references therein.