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Volumn 14, Issue 36, 2008, Pages 11512-11528

Stereoselective alcohol silylation by dehydrogenative Si-O coupling: Scope, limitations, and mechanism of the Cu-H-catalyzed non-enzymatic kinetic resolution with silicon-stereogenic silanes

Author keywords

Alcohols asymmetric catalysis; Copper; Kinetic resolution; Silicon

Indexed keywords

ATOMIC PHYSICS; ATOMS; CATALYSIS; COPPER; LIGANDS; NONMETALS; ORGANIC POLYMERS; SILANES; SUBSTRATES;

EID: 57649224066     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200801377     Document Type: Article
Times cited : (75)

References (90)
  • 2
    • 0003405157 scopus 로고    scopus 로고
    • 3rd ed, Thieme, Stuttgart
    • b) P. J. Kocieñsky, Protecting Groups, 3rd ed., Thieme, Stuttgart, 2004, pp. 188-230.
    • (2004) Protecting Groups , pp. 188-230
    • Kocieñsky, P.J.1
  • 3
    • 84891001254 scopus 로고    scopus 로고
    • For reviews, see: a, Eds, P. G. Andersson, I.J. Munslow, Wiley-VCH, Weinheim
    • For reviews, see: a) S. Rendler, M. Oestreich in Modern Reduction Methods (Eds.: P. G. Andersson, I.J. Munslow), Wiley-VCH, Weinheim, 2008, pp. 183-207;
    • (2008) Modern Reduction Methods , pp. 183-207
    • Rendler, S.1    Oestreich, M.2
  • 6
    • 0000421290 scopus 로고    scopus 로고
    • Eds, E.N. Jacobsen, A. Pfaltz, H. Yamamoto, Springer, Berlin
    • d) H. Nishiyama in Comprehensive Asymmetric Catalysis, Vol. 1 (Eds.: E.N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, pp. 267-288.
    • (1999) Comprehensive Asymmetric Catalysis , vol.1 , pp. 267-288
    • Nishiyama, H.1
  • 8
    • 57649166595 scopus 로고    scopus 로고
    • For a brief summary, see
    • For a brief summary, see: S. Rendler, M. Oestreich, Angew. Chem. 2008, 120, 254-257;
    • (2008) Angew. Chem , vol.120 , pp. 254-257
    • Rendler, S.1    Oestreich, M.2
  • 9
    • 38049036289 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 248-250.
    • (2008) Angew. Chem. Int. Ed , vol.47 , pp. 248-250
  • 10
    • 57649239027 scopus 로고    scopus 로고
    • Cu-H-catalyzed silylation of secondary alcohols: S. Rendler, G. Auer, M. Oestreich, Angew. Chem. 2005, 117, 7793-7797;
    • a) Cu-H-catalyzed silylation of secondary alcohols: S. Rendler, G. Auer, M. Oestreich, Angew. Chem. 2005, 117, 7793-7797;
  • 11
    • 28244473021 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 7620-7624;
    • (2005) Angew. Chem. Int. Ed , vol.44 , pp. 7620-7624
  • 12
    • 41549107592 scopus 로고    scopus 로고
    • Cu-H-catalyzed silylation of tertiary alcohols: B. Karatas, S. Rendler, R. Fröhlich, M. Oestreich, Org. Biomol. Chem. 2008, 6, 1435-1440;
    • b) Cu-H-catalyzed silylation of tertiary alcohols: B. Karatas, S. Rendler, R. Fröhlich, M. Oestreich, Org. Biomol. Chem. 2008, 6, 1435-1440;
  • 13
    • 57649244083 scopus 로고    scopus 로고
    • Rh-H-catalyzed silylation of secondary alcohols: H. F. T. Klare, M. Oestreich, Angew. Chem. 2007, 119, 9496-9499;
    • c) Rh-H-catalyzed silylation of secondary alcohols: H. F. T. Klare, M. Oestreich, Angew. Chem. 2007, 119, 9496-9499;
  • 14
    • 37349102738 scopus 로고    scopus 로고
    • Angew. Chem Int. Ed. 2007, 46, 9335-9338.
    • (2007) Angew. Chem Int. Ed , vol.46 , pp. 9335-9338
  • 15
    • 33748413162 scopus 로고    scopus 로고
    • Catalyst-controlled silylation of meso diols: Y. Zhao, J. Rodrigo, A. H. Hoveyda, M. L. Snapper, Nature 2006, 443, 67-70;
    • a) Catalyst-controlled silylation of meso diols: Y. Zhao, J. Rodrigo, A. H. Hoveyda, M. L. Snapper, Nature 2006, 443, 67-70;
  • 16
    • 57649244080 scopus 로고    scopus 로고
    • catalystcontrolled kinetic resolution of racemic diols: Y. Zhao, A. W. Mitra, A. H. Hoveyda, M. L. Snapper, Angew. Chem. 2007, 119, 8623-8626;
    • b) catalystcontrolled kinetic resolution of racemic diols: Y. Zhao, A. W. Mitra, A. H. Hoveyda, M. L. Snapper, Angew. Chem. 2007, 119, 8623-8626;
  • 17
    • 36148978554 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 8471-8474.
    • (2007) Angew. Chem. Int. Ed , vol.46 , pp. 8471-8474
  • 19
    • 21344465658 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 3974-4001;
    • (2005) Angew. Chem. Int. Ed , vol.44 , pp. 3974-4001
  • 21
    • 84889419927 scopus 로고    scopus 로고
    • Eds, K. Mikami, M. Lautens, Wiley, New York
    • a) T. Rovis in New Frontiers in Asymmetric Catalysis (Eds.: K. Mikami, M. Lautens), Wiley, New York, 2007, pp. 275-311;
    • (2007) New Frontiers in Asymmetric Catalysis , pp. 275-311
    • Rovis, T.1
  • 26
    • 5644221512 scopus 로고    scopus 로고
    • II: C.N. Scott, C.S. Wilcox, Synthesis 2004, 2273-2276;
    • II: C.N. Scott, C.S. Wilcox, Synthesis 2004, 2273-2276;
  • 27
    • 4143116942 scopus 로고    scopus 로고
    • I: R. L. Miller, S. V. Maifeld, D. Lee, Org. Lett. 2004, 6, 2773-2776;
    • I: R. L. Miller, S. V. Maifeld, D. Lee, Org. Lett. 2004, 6, 2773-2776;
  • 28
    • 18844408347 scopus 로고    scopus 로고
    • I: H. Ito, A. Watanabe, M. Sawamura, Org. Lett. 2005, 7, 1869-1871;
    • I: H. Ito, A. Watanabe, M. Sawamura, Org. Lett. 2005, 7, 1869-1871;
  • 29
    • 22344448563 scopus 로고    scopus 로고
    • I: H. Ito, K. Takagi, T. Miyahara, M. Sawamura, Org. Lett. 2005, 7, 3001-3004;
    • I: H. Ito, K. Takagi, T. Miyahara, M. Sawamura, Org. Lett. 2005, 7, 3001-3004;
  • 30
    • 33749361506 scopus 로고    scopus 로고
    • II: Y. Gunji, Y. Yamashita, T. Ikeno, T. Yamada, Chem. Lett. 2006, 714-715.
    • II: Y. Gunji, Y. Yamashita, T. Ikeno, T. Yamada, Chem. Lett. 2006, 714-715.
  • 31
    • 57649205752 scopus 로고    scopus 로고
    • Review on the related Cu-H-catalyzed carbonyl reduction: S. Rendler, M. Oestreich, Angew. Chem. 2007, 119, 504-510;
    • Review on the related Cu-H-catalyzed carbonyl reduction: S. Rendler, M. Oestreich, Angew. Chem. 2007, 119, 504-510;
  • 32
    • 33846485125 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 498-504.
    • (2007) Angew. Chem. Int. Ed , vol.46 , pp. 498-504
  • 34
    • 0033552259 scopus 로고    scopus 로고
    • A closely related σ-bond metathesis has been suggested earlier: D. H. Appella, Y. Moritani, R. Shintani, E. M. Ferreira, S. L. Buchwald, J. Am. Chem. Soc. 1999, 121, 9473-9474.
    • A closely related σ-bond metathesis has been suggested earlier: D. H. Appella, Y. Moritani, R. Shintani, E. M. Ferreira, S. L. Buchwald, J. Am. Chem. Soc. 1999, 121, 9473-9474.
  • 38
    • 17044375112 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 1661-1664;
    • (2005) Angew. Chem. Int. Ed , vol.44 , pp. 1661-1664
  • 54
    • 57649239244 scopus 로고    scopus 로고
    • It must be noted that this correlation only holds true if both reactions-with racemic as well as enantiopure silane-follow identical kinetics
    • It must be noted that this correlation only holds true if both reactions-with racemic as well as enantiopure silane-follow identical kinetics.
  • 55
    • 57649193277 scopus 로고    scopus 로고
    • [20b] see Supporting Information for details.
    • [20b] see Supporting Information for details.
  • 61
    • 13744258949 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 938-941.
    • (2005) Angew. Chem. Int. Ed , vol.44 , pp. 938-941
  • 62
    • 57649177871 scopus 로고    scopus 로고
    • [20b]
    • [20b]
  • 65
    • 57649244147 scopus 로고    scopus 로고
    • In our hands, the determination of conversion by 1H NMR spectroscopy from the crude reaction mixture emerged as a critical point. The deviation from the given values is about ±3% and might account for occasional inconsistencies in Tables 4-7
    • 1H NMR spectroscopy from the crude reaction mixture emerged as a critical point. The deviation from the given values is about ±3% and might account for occasional inconsistencies in Tables 4-7.
  • 66
    • 57649201755 scopus 로고    scopus 로고
    • Reductive cleavage of silyl ethers proceeds under retention of configuration at silicon: M. Oestreich, G. Auer, M. Keller, Eur. J. Org. Chem. 2005, 184-195.
    • Reductive cleavage of silyl ethers proceeds under retention of configuration at silicon: M. Oestreich, G. Auer, M. Keller, Eur. J. Org. Chem. 2005, 184-195.
  • 68
    • 0029617354 scopus 로고    scopus 로고
    • Selected examples for enzymatic kinetic resolutions of pyridyl methanols: a By oxidation: M. Takemoto, K. Achiwa, Tetrahedron: Asymmetry 1995, 6, 2925-2928;
    • Selected examples for enzymatic kinetic resolutions of pyridyl methanols: a) By oxidation: M. Takemoto, K. Achiwa, Tetrahedron: Asymmetry 1995, 6, 2925-2928;
  • 69
    • 0000506063 scopus 로고    scopus 로고
    • by acylation: J. Uenishi, T. Hiraoka, S. Hata, K. Nishikawi, O. Yonemitsu, K. Nakamura, H. Tsukube, J. Org. Chem. 1998, 63, 2481-2487.
    • b) by acylation: J. Uenishi, T. Hiraoka, S. Hata, K. Nishikawi, O. Yonemitsu, K. Nakamura, H. Tsukube, J. Org. Chem. 1998, 63, 2481-2487.
  • 72
    • 57649239245 scopus 로고    scopus 로고
    • TURBOMOLE Ver. 5.9, University of Karlsruhe, 2006
    • TURBOMOLE (Ver. 5.9); University of Karlsruhe, 2006 (http://www.turbomole.com).
  • 77
    • 0039209924 scopus 로고    scopus 로고
    • A. Schäfer, C. Huber, R. Ahlrichs, J. Chem. Phys. 1994, 100, 5829-5835. For TZVPP, additional functions of higher angular momentum are added. Contradictions: Cu: [6s4p3d1f], P: [5s5p2d1f], O: [5s3p2d1f], H: [3s2pld], C: [5s3p2d1f], Si: [5s5p2d1f] (basis set from ftp.chemie.uni-karlsruhe.de/pub/).
    • A. Schäfer, C. Huber, R. Ahlrichs, J. Chem. Phys. 1994, 100, 5829-5835. For TZVPP, additional functions of higher angular momentum are added. Contradictions: Cu: [6s4p3d1f], P: [5s5p2d1f], O: [5s3p2d1f], H: [3s2pld], C: [5s3p2d1f], Si: [5s5p2d1f] (basis set from ftp.chemie.uni-karlsruhe.de/pub/).
  • 83
    • 1542707483 scopus 로고    scopus 로고
    • L1d: G.P. Schiemenz, K. Röhlk, Chem. Ber. 1971, 104, 1219-1233;
    • c) L1d: G.P. Schiemenz, K. Röhlk, Chem. Ber. 1971, 104, 1219-1233;
  • 84
    • 0000039347 scopus 로고    scopus 로고
    • L1f: J. Porwisiak, M. Schlosser, Chem. Ber. 1996, 129, 233-235.
    • d) L1f: J. Porwisiak, M. Schlosser, Chem. Ber. 1996, 129, 233-235.
  • 90
    • 0003562849 scopus 로고    scopus 로고
    • University of Freiburg Germany
    • E. Keller, SCHAKAL, University of Freiburg (Germany), 1997.
    • (1997) SCHAKAL
    • Keller, E.1


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