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(d) Noyori, R.; Ikeda, T.; Ohkuma, T.; Widhalm, M.; Kitamura, M.; Takaya, H.; Akutagawa, S.; Sayo, N.; Saito, T.; Taketomi, T.; Kumobayashi, H. J. Am. Chem. Soc. 1989, 111, 9134.
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For further reading of this antagonist, see: Norman, M. H.; Chen, N.; Chen, Z.; Fotsch, C.; Hale, C.; Han, N.; Hurt, R.; Jenkins, T.; Kincaid, J.; Liu, L.; Lu, Y.; Moreno, O.; Santora, V. J.; Sonnenberg, J. D.; Karbon, W. J. Med. Chem. 2000, 43, 4288.
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Turnbull, A. V.; Ellershaw, L.; Masters, D. J.; Birtles, S.; Boyer, S.; Carroll, D.; Clarkson, P.; Loxham, S. J. G.; McAulay, P.; Teague, J. L.; Foote, K. M.; Pease, J. E.; Block, M. H. Diabetes 2002, 51, 2441.
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0019168718
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49149144714
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(b) Melillo, D. G.; Shinkai, I.; Liu, T.; Ryan, K.; Sletzinger, M. Tetrahedron Lett. 1980, 21, 2783.
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(c) Lee, S.-H.; Yoshida, K.; Matsushita, H.; Clapham, B.; Koch, G.; Zimmermann, J.; Janda, K. D. J. Org. Chem. 2004, 69, 8829.
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(e) Davies, J. R.; Kane, P. D.; Moody, C. J. Tetrahedron 2004, 60, 3967.
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(f) Bashford, K. E.; Cooper, A. L.; Kane, P. D.; Moody, C. J.; Muthusamy, S.; Swann, E. J. Chem. Soc., Perkin Trans. 1 2002, 1672.
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(g) Lee, S.-H.; Clapham, B.; Zimmermann, J.; Janda, K. D. Org. Lett. 2003, 5, 511.
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20
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33645480748
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-
note
-
Pd(II), Co(II), Cu(I), Ni(II) and Rh(II) were tried. Besides Rh(II), no other metal gave satisfying results. No conversion was observed for Co(II) and Cu(I). Pd(II) and Ni(II) only afforded 10% yield in the initial studies, whereas Rh(II) gave roughly 70% yield.
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-
-
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21
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0037034126
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For examples on the use of phenol to accelerate Rh(II)-catalyzed insertion reactions, see: (a) Yamazaki, K.; Kondo, Y. Chem. Commun. 2002, 210.
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Yamazaki, K.1
Kondo, Y.2
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23
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0037418806
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For the insertion of α-diazo-β-ketoesters into aromatic C-H bonds, see: Tsutsui, H.; Yamaguchi, Y.; Kitagaki, S.; Nakamura, S.; Anada, M.; Hashimoto, S. Tetrahedron: Asymmetry 2003, 14, 817.
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Tetrahedron: Asymmetry
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Tsutsui, H.1
Yamaguchi, Y.2
Kitagaki, S.3
Nakamura, S.4
Anada, M.5
Hashimoto, S.6
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24
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1842663163
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For an example on slow addition of the diazo compound see: Davies, J. R.; Kane, P. D.; Moody, C. J. Tetrahedron 2004, 60, 3967.
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Tetrahedron
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Davies, J.R.1
Kane, P.D.2
Moody, C.J.3
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26
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33645478099
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note
-
No O-H insertion product could be isolated from entry 11 in Table 1. Therefore the presence of O-H insertion product is believed to be due to the presence of an amide in the para position.
-
-
-
-
27
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33645488585
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Wiley: New York
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For an easy and efficient synthesis of α-diazo-β-keto-esters see, for example: (a) Davies, H. M. L.; Cantrell, W. R. Jr.; Romines, K. R.; Baum, J. S. Org. Synth. Coll. Vol. 9; Wiley: New York, 1998, 422.
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Davies, H.M.L.1
Cantrell Jr., W.R.2
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Baum, J.S.4
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0001844889
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(b) Davies, H. M. L.; Cantrell, W. R. Jr.; Romines, K. R.; Baum, J. S. Org. Synth. 1992, 70, 93.
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(c) Moody, C. J.; Slawin, A. M. Z.; Willows, D. Org. Biomol. Chem. 2003, 1, 2716.
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30
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0028272257
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For another example of β-hydride elimination, see: Cox, G. G.; Haigh, D.; Hindley, R. M.; Miller, D. J.; Moody, C. J. Tetrahedron Lett. 1994, 35, 3139.
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Moody, C.J.5
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