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(4S,5S)-4f and (4R,5S)-4f can be separated by column chromatography. Interestingly, 2f and 3f have been obtained from trans-cinnamalde-hyde, the only compound used in this work with the carbonyl function not directly attached to the aromatic ring.
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(4S,5S)-4f and (4R,5S)-4f can be separated by column chromatography. Interestingly, 2f and 3f have been obtained from trans-cinnamalde-hyde, the only compound used in this work with the carbonyl function not directly attached to the aromatic ring.
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Crystal data for (5S,6S)-10a: single crystals were obtained by crystallization from ethyl acetate/hexane. A single crystal of 10a compound was subjected to X-ray diffraction studies on a Seifert 3003 SC rotating anode diffractometer with (Cu Kα) radiation (graphite monochromator) using 2θ-ω) scans at 293(2) K. Crystal data for 10a: C13H15N1O3, M, 233.26, triclinic, space group PI (No. 1, a, 5.7310(11) Å, b, 9.956(2) Å, c, 11.765(2) Å, α, 106.35(3)°, β, 96.43(3)°, γ, 100.74(3)°, V, 623.1(2) Å3, Z, 2, Dc, 1.243 mg/m3, m, Cu Kα, 0.726 mm -1, F(000, 248; 1081 reflections were collected at 4.75 ≤ 2theta; ≤ 59.85, of which 1612 with I > 2σ(I) were considered to be observed. The structure was determined by direct methods using the SHELXTL suite of programs. Full-ma
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2 = 0.1213. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-608236. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, U.K. (fax: (+44)1223-336-033;e-mail: deposit@ccdc.cam.ac.uk).
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To our knowledge, this is the first example of O,O-allylic rearrangement followed by Claisen rearrangement and Michael addition, promoted by lithium amide. The allylic acetate rearrangement is well documented in basic medium (see refs 17 and 18), with Pd(II) (see Overman, L. E. Angew. Chem., Int. Ed Eng. 1984, 23, 579-586) or TMSOTf as catalyst (see Basavaiah, D.; Muthukumaran, K.; Sreenivasulu, B. Synthesis, 2001, 545-548). For anionic O,N-carbamate allylic rearrangement see ref 18.
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To our knowledge, this is the first example of O,O-allylic rearrangement followed by Claisen rearrangement and Michael addition, promoted by lithium amide. The allylic acetate rearrangement is well documented in basic medium (see refs 17 and 18), with Pd(II) (see Overman, L. E. Angew. Chem., Int. Ed Eng. 1984, 23, 579-586) or TMSOTf as catalyst (see Basavaiah, D.; Muthukumaran, K.; Sreenivasulu, B. Synthesis, 2001, 545-548). For anionic O,N-carbamate allylic rearrangement see ref 18.
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