Catalytic Enantioselective Isomerization of Silacyclopentene Oxides: New Strategy for Stereocontrolled Assembly of Acyclic Polyols
2001; Wiley; Volume: 40; Issue: 24 Linguagem: Inglês
10.1002/1521-3773(20011217)40
ISSN1521-3773
Autores Tópico(s)Organoboron and organosilicon chemistry
ResumoAngewandte Chemie International EditionVolume 40, Issue 24 p. 4757-4759 Communication Catalytic Enantioselective Isomerization of Silacyclopentene Oxides: New Strategy for Stereocontrolled Assembly of Acyclic Polyols Dong Liu, Dong Liu Department of Chemistry University of Chicago 5735 South Ellis Avenue Chicago, IL 60637, USA, Fax: (+1) 773-702-0805Search for more papers by this authorSergey A. Kozmin Prof. Dr., Sergey A. Kozmin Prof. Dr. [email protected] Department of Chemistry University of Chicago 5735 South Ellis Avenue Chicago, IL 60637, USA, Fax: (+1) 773-702-0805Search for more papers by this author Dong Liu, Dong Liu Department of Chemistry University of Chicago 5735 South Ellis Avenue Chicago, IL 60637, USA, Fax: (+1) 773-702-0805Search for more papers by this authorSergey A. Kozmin Prof. Dr., Sergey A. Kozmin Prof. Dr. [email protected] Department of Chemistry University of Chicago 5735 South Ellis Avenue Chicago, IL 60637, USA, Fax: (+1) 773-702-0805Search for more papers by this author First published: 18 December 2001 https://doi.org/10.1002/1521-3773(20011217)40:24 3.0.CO;2-SCitations: 45 Initial funding of this work was provided by the University of Chicago. We are grateful to the donors of the Petroleum Research Fund for further financial support. Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Graphical Abstract A versatile precursor for the assembly of a range of polyol-containing fragments is the silacyclic alcohol 2 that results from the highly enantioselective, catalytic isomerization of diphenylsilacyclopentene oxide (1). The use of this precusor is illustrated with the efficient and highly diastereoselective assembly of acyclic tetraol motifs. References 1 1a T.-L. Ho, Symmetry: A Basis for Synthetic Design, Wiley, New York, 1995; 1b R. S. Ward, Chem. Soc. Rev. 1990, 19, 1; 1c M. C. Wills, J. Chem. Soc. Perkin Trans. 1 1999, 1765. 2 For selected examples of catalytic enantioselective desymmetrizations, see: 2a S. L. Schreiber, T. S. Schreiber, D. B. Smith, J. Am. Chem. Soc. 1987, 109, 1525; 2b W. A. Nugent, J. Am. Chem. Soc. 1992, 114, 2768; 2c L. E. Martinez, J. L. Leighton, D. H. Carsten, E. N. Jacobsen, J. Am. Chem. Soc. 1995, 117, 5897; 2d T. Iida, N. Yamamoto, H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 1997, 119, 4783; 2e M. Lautens, T. Rovis, J. Am. Chem. Soc. 1997, 119, 11 090; 2f S. E. Denmark, P. A. Barsanti, K. T. Wong, R. A. Stavenger, J. Org. Chem. 1998, 63, 2428; 2g T. Oriyama, K. Imai, T. Sano, T. Hosoya, Tetrahedron Lett. 1998, 39, 397; 2h S. L. Aeilts, D. R. Cefalo, P. J. Bonitatebus, J. H. Houser, A. H. Hoveyda, R. R. Schrock, Angew. Chem. 2001, 113, 1500; Angew. Chem. Int. Ed. 2001, 40, 1452. 3 For the use of cyclic siloxanes in stereoselective synthesis, see: 3a K. Tamao, T. Nakajima, R. Sumiiya, H. Arai, N. Higuchi, Y. Ito, J. Am. Chem. Soc. 1986, 108, 6090; 3b S. H. Bergens, P. Noheda, J. Whelan, B. Bosnich, J. Am. Chem. Soc. 1992, 114, 2121; 3c M. R. Hale, A. H. Hoveyda, J. Org. Chem. 1992, 57, 1643; 3d M. J. Zacuto, J. L. Leighton, J. Am. Chem. Soc. 2000, 122, 8587; For the use of siliranes, see: 3e W. S. Palmer, J. T. Shaw, J. H. Smitrovich, J. D. Sonnenberg, A. L. Presley, K. A. Woerpel, J. Am. Chem. Soc. 1995, 117, 10 575, and references therein. 4 For reviews on preparation and properties of cyclic silanes, see: 4a J. Hermanns, B. Schmidt, J. Chem. Soc. Perkin. Trans. 1 1998, 2209; 4b J. Hermanns, B. Schmidt, J. Chem. Soc. Perkin. Trans. 1 1999, 81. 5 J. K. Whitesell, S. W. Felman, J. Org. Chem. 1980, 45, 755. 6 For reviews, see: 6a J. K. Crandall, M. Apparu, Org. React. 1983, 29, 345; 6b A. R. Gibbs, G. P. Lee, Tetrahedron 1996, 52, 14 361; 6c P. O'Brien, J. Chem. Soc. Perkin Trans. 1 1998, 1439. 7 For a pioneering investigation on catalytic enantioselective isomerization of carbocyclic epoxides, see: M. Asami, T. Ishizaki, S. Inoue, Tetrahedron: Asymmetry 1994, 5, 793. 8 8a W. J. Richter, Synthesis 1982, 1102; 8b S. Mignani, D. Damour, J.-P. Bastart, G. Manuel, Syn. Commun. 1995, 25, 3855. 9 G. Manuel, R. Boukherroub, J. Organomet. Chem. 1993, 447, 167. 10 10a M. J. Södergren, P. G. Andersson, J. Am. Chem. Soc. 1998, 120, 10 760; 10b M. J. Södergren, S. K. Bertilsson, P. G. Andersson, J. Am. Chem. Soc. 2000, 122, 6610. 11 Determination of the enantiomeric excess was carried out by the Mosher ester 1H NMR analysis; see Supporting Information for details. The attempts to resolve alcohol 3 a using six different chiral HPLC stationary phases proved unsuccessful. 12 The absolute configuration of silane (R)-3 a was later confirmed by its conversion to the known (S)-triol 9, as illustrated below. 13 K. Tamao, E. Nakajo, Y. Ito, J. Org. Chem. 1987, 52, 4414. 14 K. Tamao, M. Kumada, K. Maeda, Tetrahedron Lett. 1984, 321. 15 I. Fleming, P. E. Sanderson, Tetrahedron Lett. 1987, 28, 4229. 16 J. H. Smitrovich, K. A. Woerpel, J. Org. Chem. 1996, 61, 6044. 17a N. Zhao, N. Berova, K. Nakanishi, M. Rohmer, P. Mougenot, U. J. Jurgens, Tetrahedron 1996, 52, 2777; 17b J. F. River-Cruz, G. Garcia-Aguirre, C. M. Cerda-Garcia-Rojas, R. Mata, Tetrahedron 2000, 56, 5337. Citing Literature Supporting Information Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2001/z17864_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. Volume40, Issue24December 17, 2001Pages 4757-4759 ReferencesRelatedInformation
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