-
2
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-
4043123499
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-
For a discussion of enantioselective palladium(II)-catalyzed reactions, see:
-
For a discussion of enantioselective palladium(II)-catalyzed reactions, see:. Tietze L., Hiriyakkanavar L., and Bell H. Chem. Rev. 104 (2004) 3453
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(2004)
Chem. Rev.
, vol.104
, pp. 3453
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Tietze, L.1
Hiriyakkanavar, L.2
Bell, H.3
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3
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34548477138
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For recent metal-catalyzed asymmetric syntheses of structurally, related indanones, see:
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-
-
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4
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33644961282
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Shintani R., Yashio K., Nakamura T., Okamoto K., Shimada T., and Hayashi T. J. Am. Chem. Soc. 128 (2006) 2772
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(2006)
J. Am. Chem. Soc.
, vol.128
, pp. 2772
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-
Shintani, R.1
Yashio, K.2
Nakamura, T.3
Okamoto, K.4
Shimada, T.5
Hayashi, T.6
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6
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34548486878
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For recent reviews, see:
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9
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0037124890
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see also:
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Mainetti E., Mouries V., Fensterbank L., Malacria M., and Marco-Contelles J. Angew. Chem., Int. Ed. 41 (2002) 2132 see also:
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(2002)
Angew. Chem., Int. Ed.
, vol.41
, pp. 2132
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-
Mainetti, E.1
Mouries, V.2
Fensterbank, L.3
Malacria, M.4
Marco-Contelles, J.5
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10
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3242713858
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Harrak Y., Blaszykowski C., Bernard M., Cariou K., Mainetti E., Mouries V., Dhimane A.L., Fensterbank L., and Malacria M. J. Am. Chem. Soc. 126 (2004) 8656
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(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 8656
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-
Harrak, Y.1
Blaszykowski, C.2
Bernard, M.3
Cariou, K.4
Mainetti, E.5
Mouries, V.6
Dhimane, A.L.7
Fensterbank, L.8
Malacria, M.9
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16
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3242691284
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For other examples of Au-mediated rearrangements of propargylic/homopropargylic esters, see:
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Mamane V., Gress T., Krause H., and Furstner A. J. Am. Chem. Soc. 126 (2004) 8654 For other examples of Au-mediated rearrangements of propargylic/homopropargylic esters, see:
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(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 8654
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-
Mamane, V.1
Gress, T.2
Krause, H.3
Furstner, A.4
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27
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34548482205
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note
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TLC evidence indicated that some ketone 8a was formed during the course of the reaction. Rautenstrauch also observed this phenomenon in the absence of AcOH and suggested that it occurred via formal loss of ketene.
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28
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34548499265
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note
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2 was optimal.
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29
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0028354822
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1H NMR shows similar peaks to that of a structurally-related 2-ethoxycyclopentadiene:
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1H NMR shows similar peaks to that of a structurally-related 2-ethoxycyclopentadiene:. Hatanaka M., Himeda Y., Imashiro R., Tanaka Y., and Ueda I. J. Org. Chem. 59 (1994) 111
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(1994)
J. Org. Chem.
, vol.59
, pp. 111
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Hatanaka, M.1
Himeda, Y.2
Imashiro, R.3
Tanaka, Y.4
Ueda, I.5
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30
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34548476682
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-
note
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Longer reaction times or higher catalyst loadings led to complex mixtures minus starting material. Crude NMR indicated that some cyclized product was likely formed, but it could not be isolated free of other compounds.
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31
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34548479677
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Classes of palladium(II) complexes examined: Pd(II)-bisoxazolines (trifluoroacetate and tetrafluoroborate derivatives); see:
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34
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0037127524
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and Pd(II)-BINAP (tetrafluoroborate derivative). In most experiments, no cyclization was observed. Instead, the reaction produced a mixture of uncyclized products. Pd(II) chloride-bisoxazoline complex did promote the rearrangement of 7a, but isolated product 8a was racemic
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Kato K., Tanaka M., Yamamoto Y., and Akita H. Tetrahedron Lett. 43 (2002) 1511 and Pd(II)-BINAP (tetrafluoroborate derivative). In most experiments, no cyclization was observed. Instead, the reaction produced a mixture of uncyclized products. Pd(II) chloride-bisoxazoline complex did promote the rearrangement of 7a, but isolated product 8a was racemic
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(2002)
Tetrahedron Lett.
, vol.43
, pp. 1511
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-
Kato, K.1
Tanaka, M.2
Yamamoto, Y.3
Akita, H.4
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35
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34548495980
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For reviews of Nazarov chemistry, see:
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40
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34548490454
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note
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A reviewer correctly pointed out that intermediate 20 could cyclize to give 23. This can also be viewed as a 4π-electrocyclization if a (zwitterionic) resonance form of the carbene is considered.
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-
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41
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34548514151
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note
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1H NMR spectra from reactions with terminal alkyne substrates revealed the presence of related compounds in trace amounts.
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43
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0001600367
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For mechanistic work concerning [1,5] H shifts in cyclopentadienes, see:
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For mechanistic work concerning [1,5] H shifts in cyclopentadienes, see:. McLean S., and Haynes P. Tetrahedron 21 (1965) 2329
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(1965)
Tetrahedron
, vol.21
, pp. 2329
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-
McLean, S.1
Haynes, P.2
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44
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0037462101
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For a recent example of asymmetric mercuriocyclization of γ-hydroxy-cis-alkenes, see:
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For a recent example of asymmetric mercuriocyclization of γ-hydroxy-cis-alkenes, see:. Kang S.H., and Kim M. J. Am. Chem. Soc. 125 (2003) 4684
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(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 4684
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Kang, S.H.1
Kim, M.2
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45
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33645005049
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Imagawa H., Fujikawa Y., Tsuchihiro A., Kinoshita A., Yoshinaga T., Takao H., and Nishizawa M. Synlett (2006) 639
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(2006)
Synlett
, pp. 639
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Imagawa, H.1
Fujikawa, Y.2
Tsuchihiro, A.3
Kinoshita, A.4
Yoshinaga, T.5
Takao, H.6
Nishizawa, M.7
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47
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34548477137
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note
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1H NMR J values for each diastereomer indicate a trans-relationship between the cyclopentenone stereocenters.
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