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Volumn 125, Issue 23, 2003, Pages 7005-7013

Mechanistic investigations of the palladium-catalyzed aerobic oxidative kinetic resolution of secondary alcohols using (-)-Sparteine

Author keywords

[No Author keywords available]

Indexed keywords

CHIRAL LIGANDS;

EID: 0038276962     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja034262n     Document Type: Article
Times cited : (129)

References (74)
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    • Kinetic resolution
    • rel = In[(1 - C)(1 - ee)]/ln[(1 - C)(1 + ee)] where C is the conversion and ee is the enantiomeric excess. For an excellent discussion of kinetic resolutions, see: Kagan, H. B.; Fiaud, J. C. Kinetic Resolution. Top. Stereochem. 1988, 18, 249.
    • (1988) Top. Stereochem. , vol.18 , pp. 249
    • Kagan, H.B.1    Fiaud, J.C.2
  • 24
    • 0000469464 scopus 로고    scopus 로고
    • Alcohols can be resolved by other methods. For catalytic acylation, see: (a) Lin, M.-H.; RajanBabu, T. V. Org. Lett. 2002, 4, 1607. (b) Vedejs, E.; MacKay, J. A. Org. Lett. 2001, 3, 535. (c) Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 2001, 123, 6496. (d) Bellemine-Laponnaz, S.; Tweddell, J.; Ruble, J. C.; Breitling, F. M.; Fu, G. C. Chem. Commun. 2000, 1009. (e) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J., Jr.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638. (f) Vedejs, E.; Daugulis, O. J. Am. Chem. Soc. 1999, 121, 5813. (g) Sano, T.; Imai, K.; Ohashi, K.; Oriyama, T. Chem. Lett. 1999, 265. (h) Miller, S. J.; Copeland, G. T.; Papaioannou, N.; Horstmann, T. E.; Ruel, E. M. J. Am. Chem. Soc. 1998, 120, 1629. (i) Ruble, J. C.; Tweddell, J.; Fu, G. C. J. Org. Chem. 1998, 63, 2794. (j) Ruble, J. C.; Latham, H. A.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 1492. (k) Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169. For epoxidation approach: (l) Martin, V. S.; Woodward, S. S.; Katsuki, T.; Yamada, Y.; Ikeda, M.; Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 6237. Using benzoylation: (m) Iwata, T.; Miyake, Y.; Nishibayashi, Y.; Uemura, S. J. Chem. Soc., Perkin Trans. 1 2002, 13, 1548.
    • (2002) Org. Lett. , vol.4 , pp. 1607
    • Lin, M.-H.1    RajanBabu, T.V.2
  • 25
    • 0000363155 scopus 로고    scopus 로고
    • Alcohols can be resolved by other methods. For catalytic acylation, see: (a) Lin, M.-H.; RajanBabu, T. V. Org. Lett. 2002, 4, 1607. (b) Vedejs, E.; MacKay, J. A. Org. Lett. 2001, 3, 535. (c) Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 2001, 123, 6496. (d) Bellemine-Laponnaz, S.; Tweddell, J.; Ruble, J. C.; Breitling, F. M.; Fu, G. C. Chem. Commun. 2000, 1009. (e) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J., Jr.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638. (f) Vedejs, E.; Daugulis, O. J. Am. Chem. Soc. 1999, 121, 5813. (g) Sano, T.; Imai, K.; Ohashi, K.; Oriyama, T. Chem. Lett. 1999, 265. (h) Miller, S. J.; Copeland, G. T.; Papaioannou, N.; Horstmann, T. E.; Ruel, E. M. J. Am. Chem. Soc. 1998, 120, 1629. (i) Ruble, J. C.; Tweddell, J.; Fu, G. C. J. Org. Chem. 1998, 63, 2794. (j) Ruble, J. C.; Latham, H. A.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 1492. (k) Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169. For epoxidation approach: (l) Martin, V. S.; Woodward, S. S.; Katsuki, T.; Yamada, Y.; Ikeda, M.; Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 6237. Using benzoylation: (m) Iwata, T.; Miyake, Y.; Nishibayashi, Y.; Uemura, S. J. Chem. Soc., Perkin Trans. 1 2002, 13, 1548.
    • (2001) Org. Lett. , vol.3 , pp. 535
    • Vedejs, E.1    MacKay, J.A.2
  • 26
    • 0034807976 scopus 로고    scopus 로고
    • Alcohols can be resolved by other methods. For catalytic acylation, see: (a) Lin, M.-H.; RajanBabu, T. V. Org. Lett. 2002, 4, 1607. (b) Vedejs, E.; MacKay, J. A. Org. Lett. 2001, 3, 535. (c) Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 2001, 123, 6496. (d) Bellemine-Laponnaz, S.; Tweddell, J.; Ruble, J. C.; Breitling, F. M.; Fu, G. C. Chem. Commun. 2000, 1009. (e) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J., Jr.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638. (f) Vedejs, E.; Daugulis, O. J. Am. Chem. Soc. 1999, 121, 5813. (g) Sano, T.; Imai, K.; Ohashi, K.; Oriyama, T. Chem. Lett. 1999, 265. (h) Miller, S. J.; Copeland, G. T.; Papaioannou, N.; Horstmann, T. E.; Ruel, E. M. J. Am. Chem. Soc. 1998, 120, 1629. (i) Ruble, J. C.; Tweddell, J.; Fu, G. C. J. Org. Chem. 1998, 63, 2794. (j) Ruble, J. C.; Latham, H. A.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 1492. (k) Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169. For epoxidation approach: (l) Martin, V. S.; Woodward, S. S.; Katsuki, T.; Yamada, Y.; Ikeda, M.; Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 6237. Using benzoylation: (m) Iwata, T.; Miyake, Y.; Nishibayashi, Y.; Uemura, S. J. Chem. Soc., Perkin Trans. 1 2002, 13, 1548.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 6496
    • Copeland, G.T.1    Miller, S.J.2
  • 27
    • 0034697763 scopus 로고    scopus 로고
    • Alcohols can be resolved by other methods. For catalytic acylation, see: (a) Lin, M.-H.; RajanBabu, T. V. Org. Lett. 2002, 4, 1607. (b) Vedejs, E.; MacKay, J. A. Org. Lett. 2001, 3, 535. (c) Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 2001, 123, 6496. (d) Bellemine-Laponnaz, S.; Tweddell, J.; Ruble, J. C.; Breitling, F. M.; Fu, G. C. Chem. Commun. 2000, 1009. (e) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J., Jr.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638. (f) Vedejs, E.; Daugulis, O. J. Am. Chem. Soc. 1999, 121, 5813. (g) Sano, T.; Imai, K.; Ohashi, K.; Oriyama, T. Chem. Lett. 1999, 265. (h) Miller, S. J.; Copeland, G. T.; Papaioannou, N.; Horstmann, T. E.; Ruel, E. M. J. Am. Chem. Soc. 1998, 120, 1629. (i) Ruble, J. C.; Tweddell, J.; Fu, G. C. J. Org. Chem. 1998, 63, 2794. (j) Ruble, J. C.; Latham, H. A.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 1492. (k) Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169. For epoxidation approach: (l) Martin, V. S.; Woodward, S. S.; Katsuki, T.; Yamada, Y.; Ikeda, M.; Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 6237. Using benzoylation: (m) Iwata, T.; Miyake, Y.; Nishibayashi, Y.; Uemura, S. J. Chem. Soc., Perkin Trans. 1 2002, 13, 1548.
    • (2000) Chem. Commun. , pp. 1009
    • Bellemine-Laponnaz, S.1    Tweddell, J.2    Ruble, J.C.3    Breitling, F.M.4    Fu, G.C.5
  • 28
    • 0033596302 scopus 로고    scopus 로고
    • Alcohols can be resolved by other methods. For catalytic acylation, see: (a) Lin, M.-H.; RajanBabu, T. V. Org. Lett. 2002, 4, 1607. (b) Vedejs, E.; MacKay, J. A. Org. Lett. 2001, 3, 535. (c) Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 2001, 123, 6496. (d) Bellemine-Laponnaz, S.; Tweddell, J.; Ruble, J. C.; Breitling, F. M.; Fu, G. C. Chem. Commun. 2000, 1009. (e) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J., Jr.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638. (f) Vedejs, E.; Daugulis, O. J. Am. Chem. Soc. 1999, 121, 5813. (g) Sano, T.; Imai, K.; Ohashi, K.; Oriyama, T. Chem. Lett. 1999, 265. (h) Miller, S. J.; Copeland, G. T.; Papaioannou, N.; Horstmann, T. E.; Ruel, E. M. J. Am. Chem. Soc. 1998, 120, 1629. (i) Ruble, J. C.; Tweddell, J.; Fu, G. C. J. Org. Chem. 1998, 63, 2794. (j) Ruble, J. C.; Latham, H. A.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 1492. (k) Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169. For epoxidation approach: (l) Martin, V. S.; Woodward, S. S.; Katsuki, T.; Yamada, Y.; Ikeda, M.; Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 6237. Using benzoylation: (m) Iwata, T.; Miyake, Y.; Nishibayashi, Y.; Uemura, S. J. Chem. Soc., Perkin Trans. 1 2002, 13, 1548.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 11638
    • Jarvo, E.R.1    Copeland, G.T.2    Papaioannou, N.3    Bonitatebus P.J., Jr.4    Miller, S.J.5
  • 29
    • 0033597606 scopus 로고    scopus 로고
    • Alcohols can be resolved by other methods. For catalytic acylation, see: (a) Lin, M.-H.; RajanBabu, T. V. Org. Lett. 2002, 4, 1607. (b) Vedejs, E.; MacKay, J. A. Org. Lett. 2001, 3, 535. (c) Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 2001, 123, 6496. (d) Bellemine-Laponnaz, S.; Tweddell, J.; Ruble, J. C.; Breitling, F. M.; Fu, G. C. Chem. Commun. 2000, 1009. (e) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J., Jr.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638. (f) Vedejs, E.; Daugulis, O. J. Am. Chem. Soc. 1999, 121, 5813. (g) Sano, T.; Imai, K.; Ohashi, K.; Oriyama, T. Chem. Lett. 1999, 265. (h) Miller, S. J.; Copeland, G. T.; Papaioannou, N.; Horstmann, T. E.; Ruel, E. M. J. Am. Chem. Soc. 1998, 120, 1629. (i) Ruble, J. C.; Tweddell, J.; Fu, G. C. J. Org. Chem. 1998, 63, 2794. (j) Ruble, J. C.; Latham, H. A.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 1492. (k) Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169. For epoxidation approach: (l) Martin, V. S.; Woodward, S. S.; Katsuki, T.; Yamada, Y.; Ikeda, M.; Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 6237. Using benzoylation: (m) Iwata, T.; Miyake, Y.; Nishibayashi, Y.; Uemura, S. J. Chem. Soc., Perkin Trans. 1 2002, 13, 1548.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 5813
    • Vedejs, E.1    Daugulis, O.2
  • 30
    • 0033246941 scopus 로고    scopus 로고
    • Alcohols can be resolved by other methods. For catalytic acylation, see: (a) Lin, M.-H.; RajanBabu, T. V. Org. Lett. 2002, 4, 1607. (b) Vedejs, E.; MacKay, J. A. Org. Lett. 2001, 3, 535. (c) Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 2001, 123, 6496. (d) Bellemine-Laponnaz, S.; Tweddell, J.; Ruble, J. C.; Breitling, F. M.; Fu, G. C. Chem. Commun. 2000, 1009. (e) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J., Jr.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638. (f) Vedejs, E.; Daugulis, O. J. Am. Chem. Soc. 1999, 121, 5813. (g) Sano, T.; Imai, K.; Ohashi, K.; Oriyama, T. Chem. Lett. 1999, 265. (h) Miller, S. J.; Copeland, G. T.; Papaioannou, N.; Horstmann, T. E.; Ruel, E. M. J. Am. Chem. Soc. 1998, 120, 1629. (i) Ruble, J. C.; Tweddell, J.; Fu, G. C. J. Org. Chem. 1998, 63, 2794. (j) Ruble, J. C.; Latham, H. A.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 1492. (k) Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169. For epoxidation approach: (l) Martin, V. S.; Woodward, S. S.; Katsuki, T.; Yamada, Y.; Ikeda, M.; Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 6237. Using benzoylation: (m) Iwata, T.; Miyake, Y.; Nishibayashi, Y.; Uemura, S. J. Chem. Soc., Perkin Trans. 1 2002, 13, 1548.
    • (1999) Chem. Lett. , pp. 265
    • Sano, T.1    Imai, K.2    Ohashi, K.3    Oriyama, T.4
  • 31
    • 0032564916 scopus 로고    scopus 로고
    • Alcohols can be resolved by other methods. For catalytic acylation, see: (a) Lin, M.-H.; RajanBabu, T. V. Org. Lett. 2002, 4, 1607. (b) Vedejs, E.; MacKay, J. A. Org. Lett. 2001, 3, 535. (c) Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 2001, 123, 6496. (d) Bellemine-Laponnaz, S.; Tweddell, J.; Ruble, J. C.; Breitling, F. M.; Fu, G. C. Chem. Commun. 2000, 1009. (e) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J., Jr.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638. (f) Vedejs, E.; Daugulis, O. J. Am. Chem. Soc. 1999, 121, 5813. (g) Sano, T.; Imai, K.; Ohashi, K.; Oriyama, T. Chem. Lett. 1999, 265. (h) Miller, S. J.; Copeland, G. T.; Papaioannou, N.; Horstmann, T. E.; Ruel, E. M. J. Am. Chem. Soc. 1998, 120, 1629. (i) Ruble, J. C.; Tweddell, J.; Fu, G. C. J. Org. Chem. 1998, 63, 2794. (j) Ruble, J. C.; Latham, H. A.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 1492. (k) Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169. For epoxidation approach: (l) Martin, V. S.; Woodward, S. S.; Katsuki, T.; Yamada, Y.; Ikeda, M.; Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 6237. Using benzoylation: (m) Iwata, T.; Miyake, Y.; Nishibayashi, Y.; Uemura, S. J. Chem. Soc., Perkin Trans. 1 2002, 13, 1548.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 1629
    • Miller, S.J.1    Copeland, G.T.2    Papaioannou, N.3    Horstmann, T.E.4    Ruel, E.M.5
  • 32
    • 0001647560 scopus 로고    scopus 로고
    • Alcohols can be resolved by other methods. For catalytic acylation, see: (a) Lin, M.-H.; RajanBabu, T. V. Org. Lett. 2002, 4, 1607. (b) Vedejs, E.; MacKay, J. A. Org. Lett. 2001, 3, 535. (c) Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 2001, 123, 6496. (d) Bellemine-Laponnaz, S.; Tweddell, J.; Ruble, J. C.; Breitling, F. M.; Fu, G. C. Chem. Commun. 2000, 1009. (e) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J., Jr.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638. (f) Vedejs, E.; Daugulis, O. J. Am. Chem. Soc. 1999, 121, 5813. (g) Sano, T.; Imai, K.; Ohashi, K.; Oriyama, T. Chem. Lett. 1999, 265. (h) Miller, S. J.; Copeland, G. T.; Papaioannou, N.; Horstmann, T. E.; Ruel, E. M. J. Am. Chem. Soc. 1998, 120, 1629. (i) Ruble, J. C.; Tweddell, J.; Fu, G. C. J. Org. Chem. 1998, 63, 2794. (j) Ruble, J. C.; Latham, H. A.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 1492. (k) Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169. For epoxidation approach: (l) Martin, V. S.; Woodward, S. S.; Katsuki, T.; Yamada, Y.; Ikeda, M.; Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 6237. Using benzoylation: (m) Iwata, T.; Miyake, Y.; Nishibayashi, Y.; Uemura, S. J. Chem. Soc., Perkin Trans. 1 2002, 13, 1548.
    • (1998) J. Org. Chem. , vol.63 , pp. 2794
    • Ruble, J.C.1    Tweddell, J.2    Fu, G.C.3
  • 33
    • 0030988976 scopus 로고    scopus 로고
    • Alcohols can be resolved by other methods. For catalytic acylation, see: (a) Lin, M.-H.; RajanBabu, T. V. Org. Lett. 2002, 4, 1607. (b) Vedejs, E.; MacKay, J. A. Org. Lett. 2001, 3, 535. (c) Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 2001, 123, 6496. (d) Bellemine-Laponnaz, S.; Tweddell, J.; Ruble, J. C.; Breitling, F. M.; Fu, G. C. Chem. Commun. 2000, 1009. (e) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J., Jr.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638. (f) Vedejs, E.; Daugulis, O. J. Am. Chem. Soc. 1999, 121, 5813. (g) Sano, T.; Imai, K.; Ohashi, K.; Oriyama, T. Chem. Lett. 1999, 265. (h) Miller, S. J.; Copeland, G. T.; Papaioannou, N.; Horstmann, T. E.; Ruel, E. M. J. Am. Chem. Soc. 1998, 120, 1629. (i) Ruble, J. C.; Tweddell, J.; Fu, G. C. J. Org. Chem. 1998, 63, 2794. (j) Ruble, J. C.; Latham, H. A.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 1492. (k) Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169. For epoxidation approach: (l) Martin, V. S.; Woodward, S. S.; Katsuki, T.; Yamada, Y.; Ikeda, M.; Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 6237. Using benzoylation: (m) Iwata, T.; Miyake, Y.; Nishibayashi, Y.; Uemura, S. J. Chem. Soc., Perkin Trans. 1 2002, 13, 1548.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 1492
    • Ruble, J.C.1    Latham, H.A.2    Fu, G.C.3
  • 34
    • 0030961223 scopus 로고    scopus 로고
    • Alcohols can be resolved by other methods. For catalytic acylation, see: (a) Lin, M.-H.; RajanBabu, T. V. Org. Lett. 2002, 4, 1607. (b) Vedejs, E.; MacKay, J. A. Org. Lett. 2001, 3, 535. (c) Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 2001, 123, 6496. (d) Bellemine-Laponnaz, S.; Tweddell, J.; Ruble, J. C.; Breitling, F. M.; Fu, G. C. Chem. Commun. 2000, 1009. (e) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J., Jr.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638. (f) Vedejs, E.; Daugulis, O. J. Am. Chem. Soc. 1999, 121, 5813. (g) Sano, T.; Imai, K.; Ohashi, K.; Oriyama, T. Chem. Lett. 1999, 265. (h) Miller, S. J.; Copeland, G. T.; Papaioannou, N.; Horstmann, T. E.; Ruel, E. M. J. Am. Chem. Soc. 1998, 120, 1629. (i) Ruble, J. C.; Tweddell, J.; Fu, G. C. J. Org. Chem. 1998, 63, 2794. (j) Ruble, J. C.; Latham, H. A.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 1492. (k) Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169. For epoxidation approach: (l) Martin, V. S.; Woodward, S. S.; Katsuki, T.; Yamada, Y.; Ikeda, M.; Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 6237. Using benzoylation: (m) Iwata, T.; Miyake, Y.; Nishibayashi, Y.; Uemura, S. J. Chem. Soc., Perkin Trans. 1 2002, 13, 1548.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 3169
    • Kawabata, T.1    Nagato, M.2    Takasu, K.3    Fuji, K.4
  • 35
    • 33845557915 scopus 로고
    • Alcohols can be resolved by other methods. For catalytic acylation, see: (a) Lin, M.-H.; RajanBabu, T. V. Org. Lett. 2002, 4, 1607. (b) Vedejs, E.; MacKay, J. A. Org. Lett. 2001, 3, 535. (c) Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 2001, 123, 6496. (d) Bellemine-Laponnaz, S.; Tweddell, J.; Ruble, J. C.; Breitling, F. M.; Fu, G. C. Chem. Commun. 2000, 1009. (e) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J., Jr.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638. (f) Vedejs, E.; Daugulis, O. J. Am. Chem. Soc. 1999, 121, 5813. (g) Sano, T.; Imai, K.; Ohashi, K.; Oriyama, T. Chem. Lett. 1999, 265. (h) Miller, S. J.; Copeland, G. T.; Papaioannou, N.; Horstmann, T. E.; Ruel, E. M. J. Am. Chem. Soc. 1998, 120, 1629. (i) Ruble, J. C.; Tweddell, J.; Fu, G. C. J. Org. Chem. 1998, 63, 2794. (j) Ruble, J. C.; Latham, H. A.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 1492. (k) Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169. For epoxidation approach: (l) Martin, V. S.; Woodward, S. S.; Katsuki, T.; Yamada, Y.; Ikeda, M.; Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 6237. Using benzoylation: (m) Iwata, T.; Miyake, Y.; Nishibayashi, Y.; Uemura, S. J. Chem. Soc., Perkin Trans. 1 2002, 13, 1548.
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 6237
    • Martin, V.S.1    Woodward, S.S.2    Katsuki, T.3    Yamada, Y.4    Ikeda, M.5    Sharpless, K.B.6
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    • note
    • When this transformation is run in open air, significant catalyst decomposition is observed.
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    • This Pd(II)/(-)-sparteine-catalyzed OKR has been reported in the synthesis of pharmaceuticals where they used a Mitsunobu inversion to access the other needed enantiomer of alcohol, see: Ali, I. S.; Sudalai, A. Tetrahedron Lett. 2002, 43, 5435.
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    • For a study of Pd(II)-catalyzed oxidation of alcohols in DMSO with rate-limiting catalyst turnover, see: Steinhoff, B. A.; Fix, S. R.; Stahl, S. S. J. Am. Chem. Soc. 2002, 124, 766.
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    • note
    • 2 X-ray crystal analysis.
  • 52
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    • note
    • 2. at 65 °C.
  • 53
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    • note
    • See Supporting Information for the plots and data analysis.
  • 54
    • 0037659034 scopus 로고    scopus 로고
    • note
    • Four reactions were analyzed simultaneously under the same reaction conditions (oxygen atmosphere and temperature fluctuations). See Supporting Information for apparatus. Conditions were slowed from the optimized synthetic conditions to enable the hand sampling of all four reactions.
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    • obs = k′[(-)-sparteine]/(k″ + [(-)-sparteine]). For the Michaelis-Menten equation, see: Walsh, C. Enzymatic Reaction Mechanisms; W. H. Freeman and Company: New York, 1979.
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    • note
    • In these studies, 4 mol % (-)-sparteine is used as low base concentration conditions, and 50 mol % is used as saturating conditions.
  • 57
    • 0037996796 scopus 로고    scopus 로고
    • note
    • For derivation of the rate law, see Supporting Information.
  • 58
    • 0037659036 scopus 로고    scopus 로고
    • note
    • obs = k′/(k″ + [(-)-sparteine HCI]), where k′ and k″ are constants. See Supporting Information for the statistical analysis.
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    • note
    • These experiments were performed using in situ IR to measure the initial rates of formation of the aldehyde products. The initial absorbencies were measured and converted to concentration of aldehyde product using the Beer-Lambert relationship. Low [(-)-sparteine] is 2 mol % for studies using in situ IR.
  • 64
    • 0037996795 scopus 로고    scopus 로고
    • note
    • For these studies, 2 mol % (-)-sparteine is used for low base concentration conditions, and 50 mol % (-)-sparteine is used for saturation conditions.
  • 65
    • 0037996803 scopus 로고    scopus 로고
    • note
    • p-Nitrobenzyl alcohol formed the aldehyde initially, but then formed another side product. Because of the determination of the rate by aldehyde formation, this substrate was not used for the Hammett plot at low [(-)-sparteine].
  • 66
    • 0038334683 scopus 로고    scopus 로고
    • note
    • For oxidations using benzyl alcohol. 15 mol % (-)-sparteine is suitable for saturation.
  • 68
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    • note
    • 2.
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    • For a manifestation of the Curtin-Hammett principle in which the minor diastereomeric adduct gives rise to the major enantiomer of product, see: Halpern, J. Science 1982, 217, 401.
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    • note
    • a = 1.8 in DMSO).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.