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(b) For organocatalytic conjugate addition reactions, see: Almasi, D.; Alonso, D. A.; Najera, C. Tetrahedron: Asymmetry 2007, 18, 299.
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The use of salicylaldehyde in domino oxa-Michael reactions for the synthesis of chromenes, coumarins, and related heterocycles has already been reviewed: Shi, Y.-L.; Shi, M. Org. Biomol. Chem. 2007, 5, 1499.
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(c) The use of salicylaldehyde in domino oxa-Michael reactions for the synthesis of chromenes, coumarins, and related heterocycles has already been reviewed: Shi, Y.-L.; Shi, M. Org. Biomol. Chem. 2007, 5, 1499.
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Liu, K.; Chougnet, A.; Woggon, W.-D. Angew. Chem. Int. Ed. 2008, 47, 5827;
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Tietze, L. F.; Stecker, F.; Zinngrebe, J.; Sommer, K. M. Chem. Eur. J. 2006, 12, 8770.
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For a different approach to diversonol, see: a
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For a different approach to diversonol, see: (a) Nising, C. F.; Ohnemüller, U. K.; Bräse, S. Angew. Chem. Int. Ed. 2006, 45, 307;
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0032500341
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The Trost group used also an asymmetric catalytic approach towards chromanes. The key step is a palladium-catalyzed etherification of phenols with allylic substrates to yield a tetrasubstituted stereogenic center and subsequent ring closure: (a) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1998, 120, 9074.
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The Trost group used also an asymmetric catalytic approach towards chromanes. The key step is a palladium-catalyzed etherification of phenols with allylic substrates to yield a tetrasubstituted stereogenic center and subsequent ring closure: (a) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1998, 120, 9074.
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(b) Trost, B. M.; Shen, H. C.; Dong, L.; Surivet, J.-P. J. Am. Chem. Soc. 2003, 125, 9276.
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(c) Trost, B. M.; Shen, H. C.; Dong, L.; Surivet, J.-P.; Sylvain, C. J. Am. Chem. Soc. 2004, 126, 11966.
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Crystal Structure Study of 4b Single-crystal X-ray diffraction studies were carried out on a Nonius KappaCCD diffractometer at 123(2) K using MoKα radiation (λ, 0.71073 Å, The structures were solved by Direct Methods (SHELXS-9713) and refinement were carried out using SHELXL-9713 (full-matrix least-squares refinement on F2, The hydrogen atoms were localized by difference electron density determination and refined using a 'riding' model (H(O, free, 4b: Colorless crystals, C14H18O4, M, 250.28, crystal size 0.50 x 0.45 x 0.40 mm, triclinic, space group P-1 (No.2, a, 5.9907(2) Å, b, 8.5207(3) Å, c, 12.4965(5) Å, α, 97.603(2)°, β, 95.458(2)°, γ, 97.465(2)°, V, 622.81(4) Å3, Z, 2, ρ(calcd, 1.335 Mg m-3, F000, 268, μ, 0.097 mm
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-3. Crystallographic data (excluding structure factors) for the structure reported in this work have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 717754 (4b). These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
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Franzén, J.; Marigo, M.; Fielenbach, D.; Wabnitz, T. C.; Kjærsgaard, A.; Jørgensen, K. A. J. Am. Chem. Soc. 2005, 127, 18296.
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Kjærsgaard, A.5
Jørgensen, K.A.6
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23
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0022971765
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For the hydrogenation of benzylic alcohols, see: a
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For the hydrogenation of benzylic alcohols, see: (a) Suzuki, M.; Kimura, Y.; Terashima, S. Bull. Chem. Soc. Jpn. 1986, 59, 3559.
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(b) Orsini, F.; Sello, G.; Travaini, E.; Di Gennaro, P. Tetrahedron: Asymmetry 2002, 13, 253.
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Couche, E.1
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12344294544
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(d) Kolarovic, A.; Berkes, D.; Baran, P.; Povazanec, F. Tetrahedron Lett. 2005, 46, 975.
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Kolarovic, A.1
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27
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62249219270
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Selected NMR Data Compound 4b: 1H NMR (400 MHz, CDCl3, δ, 1.42 (s, 3 H, 1.57 (dd, J, 13.5, 9.8 Hz, 1 H, 1.67 (td, J, 13.5 Hz, 1 H, 2.06-2.14 (m, 2 H, 2.28 (s, 3 H, 3.70 (s, 3 H, 3.86-3.90 (m, 1 H, 4.89 (mc, 1 H, 5.25 (mc, 1 H, 6.13 (s, 1 H, 6.24 (s, 1 H, 13C NMR (100 MHz, CDCl 3, δ, 21.9, 28.6, 34.7, 45.5, 55.4, 61.9, 73.9, 89.9, 102.9, 105.9, 108.5, 140.3, 156.2, 157.1. Compound 9b: 1H NMR (400 MHz, CDCl3, δ, 1.21-1.30 (m, 2 H, 1.28 (t, J, 7.3 Hz, 3 H, 2.04 (s, 3 H, 2.28 (s, 3 H, 2.59 (ddd, J, 14.1, 8.0, 1.3 Hz, 1 H, 2.72 (ddd, J, 14.1, 7.3, 1.3 Hz, 1 H, 3.26 (br s, 1 H, 3.86 (s, 3 H, 4.18 (q, J, 7.3 Hz, 2 H, 4.97 (dd, J, 5.8, 5.3 Hz, 1 H, 5.87 (ddd, J, 15.5, 1.3, 1.3 Hz, 1 H, 6.29 (s, 1 H, 6.35 (s, 1 H, 7.02 ddd, J, 15.5, 7.8, 7.8 Hz, 1 H, 13C NM
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3): δ = 18.3, 22.4, 25.5, 30.2, 35.9, 56.1, 78.2, 105.4, 108.2, 108.7, 111.2, 147.1, 160.2, 160.6, 180.3, 182.0.
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28
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84895308158
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Other Dieckmann condensations generating a 6-6 ring system: (a) Fu, X.; Pechacek, J. T.; Smith, D. L.; Wheeler, D. M. S. Nat. Prod. Lett. 1992, 1, 213.
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Other Dieckmann condensations generating a 6-6 ring system: (a) Fu, X.; Pechacek, J. T.; Smith, D. L.; Wheeler, D. M. S. Nat. Prod. Lett. 1992, 1, 213.
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(b) Hill, C. L.; McGrath, M.; Hunt, T.; Grogan, G. Synlett 2006, 309.
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Hill, C.L.1
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Hunt, T.3
Grogan, G.4
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