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Volumn , Issue 20, 2006, Pages 3498-3500

Lewis acid promoted rearrangements of 1,3-dioxolanyl-substituted 1,2-oxazines into novel products with 1,3,6-trioxa-7-azacyclopenta[cd]indene skeletons

Author keywords

1,2 alkyl shifts; 1,2 oxazines; Furans; Heterocycles; Hydrogenations; Lewis acids; Rearrangements

Indexed keywords

1,2 OXAZINE DERIVATIVE; 1,3,6 TRIOXA 7 AZACYCLOPENTA[CD]INDENE; 5,6 DIHYDRO 4H 1,2 OXAZINE DERIVATIVE; INDENE DERIVATIVE; LEWIS ACID; OXAZINE DERIVATIVE; TETRAHYDROFURAN; UNCLASSIFIED DRUG;

EID: 33846484299     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-956463     Document Type: Article
Times cited : (9)

References (25)
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    • Brüdgam, I.; Hartl, H., Institut für Chemie und Biochemie, Freie Universität Berlin, unpublished results.
    • Brüdgam, I.; Hartl, H., Institut für Chemie und Biochemie, Freie Universität Berlin, unpublished results.
  • 6
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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
    • 4: 305.16272; found: 305.16366.
  • 7
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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
    • 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.
    • (1984) Top. Curr. Chem , vol.116-117 , pp. 267
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  • 10
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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).
    • 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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    • 1149. For selected recent publications of our group, see
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    • 2074. Selected contributions of other groups, see
    • (g) Schmidt, E.; Reissig, H.-U.; Zimmer, R. Synthesis 2006, 2074. Selected contributions of other groups, see:
    • (2006) Synthesis
    • Schmidt, E.1    Reissig, H.-U.2    Zimmer, R.3
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