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2
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33846509764
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Angew. Chem. 2005, 117, 6383.
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Chem
, vol.117
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Angew1
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4
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16244405908
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(b) Helms, M.; Schade, W.; Pulz, R.; Watanabe, T.; Al-Harrasi, A.; Fisera, L.; Hlobilova, I.; Zahn, G.; Reissig, H.-U. Eur. J. Org. Chem. 2005, 1003.
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(2005)
Eur. J. Org. Chem
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Helms, M.1
Schade, W.2
Pulz, R.3
Watanabe, T.4
Al-Harrasi, A.5
Fisera, L.6
Hlobilova, I.7
Zahn, G.8
Reissig, H.-U.9
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5
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33846557317
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Brüdgam, I.; Hartl, H., Institut für Chemie und Biochemie, Freie Universität Berlin, unpublished results.
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Brüdgam, I.; Hartl, H., Institut für Chemie und Biochemie, Freie Universität Berlin, unpublished results.
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6
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33846545491
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Typical Procedure, Conversion of syn-1b into 5. SnCl4 (0.78 mL) was added to a solution of syn-1b (0.65 g, 2.13 mmol) in MeCN (18 mL) at -30 °C. The mixture was allowed to warm up to 0 °C within 3 h, then stirred for an additional 5 h at r.t, H2O (32 mL) was added and the mixture was extracted with CH2Cl2. The combined organic extracts were dried (Na2SO4) and concentrated. The residue was purified by column chromatography (silica gel, hexane-EtOAc, 2:1) to give 5 (0.44 g, 68, as a colorless oil. Analytical Data for (4aR,7aS,7b5)-7-Benzyl-7b-methoxy-4,4-dimethylhexahydro- 2//,4//-l,3>6-trioxa-7-azacyclopenta[cd]indene, α] D22 +4.8 (c 0.42, CHCl3, 1H NMR (500 MHz, CDCl3, δ, 1.35, 1.41 (2s, 3 H each, Me, 2.15 (dd, J, 1.1, 5.1 Hz, 1 H, 4a-H, 3.42 (s, 3 H, OMe, 3.85 dd, J, 4.6, 10.4 Hz, 1 H
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4: 305.16272; found: 305.16366.
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7
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0013570850
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Review concerning 1,2-sigmatropic shifts of alkyl groups: a, the rearrangement described here has some similarities to the pinacol rearrangement
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Review concerning 1,2-sigmatropic shifts of alkyl groups: (a) Shubin, V. G. Top. Curr. Chem. 1984, 116-117, 267; the rearrangement described here has some similarities to the pinacol rearrangement.
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(1984)
Top. Curr. Chem
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, pp. 267
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Shubin, V.G.1
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8
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30144436554
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For Prins-pinacol tandem reactions, see
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(b) For Prins-pinacol tandem reactions, see: Lavigne, R. M. A.; Riou, M.; Girardin, M.; Morency, L.; Barriault, L. Org. Lett. 2005, 7, 5921.
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Org. Lett
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Lavigne, R.M.A.1
Riou, M.2
Girardin, M.3
Morency, L.4
Barriault, L.5
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10
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33846487303
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In case of a p-methoxybenzyloxy substituent fragmentation leading to bicyclic ketone 4 was observed (Pfrengle, F.; Reissig, H.-U. unpublished results).
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In case of a p-methoxybenzyloxy substituent fragmentation leading to bicyclic ketone 4 was observed (Pfrengle, F.; Reissig, H.-U. unpublished results).
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11
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33846471630
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Helms, M. Dissertation; Freie Universität Berlin: Germany, 2005.
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Helms, M. Dissertation; Freie Universität Berlin: Germany, 2005.
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14
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0036602415
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1149. For selected recent publications of our group, see
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(c) Tsoungas, P. G. Heterocycles 2002, 57, 1149. For selected recent publications of our group, see:
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Heterocycles
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Tsoungas, P.G.1
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0033915384
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Pulz, R.; Watanabe, T.; Schade, W.; Reissig, H.-U. Synlett 2000, 983.
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Pulz, R.1
Watanabe, T.2
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(e) Pulz, R.; Al-Harrasi, A.; Reissig, H.-U. Org. Lett. 2002, 4, 2353.
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(2002)
Org. Lett
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Pulz, R.1
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(f) Pulz, R.; Cicchi, S.; Brandi, A.; Reissig, H.-U. Eur. J. Org. Chem. 2003, 1153.
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(2003)
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Pulz, R.1
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33846543721
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Angew. Chem. 2003, 115, 3131.
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(2003)
Chem
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Angew. Chem. 2005, 117, 8042.
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