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The X-ray analysis was performed from the crystalline state of the ketal product: (7a′ S*)-7a′-prop-2″-ynyl-1′,2′, 4′,6′,7′,7a′-hexahydrospiro[1,3-dioxolan-2, 5′-indene] (see also N. T. Tzvetkov, PhD Thesis, University of Bielefeld, Germany, 2005).
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52
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31144434494
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note
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Corey cyclopropanation of the compound 5 resulted predominantly in the formation of a 93:7 diastereomeric mixture of trans-and cis-oxirane products.
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53
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31144479516
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CCDC-276396 (rac-18) contains the supplementary crystallographic data for this paper. 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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55
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0037629739
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The structure of rac-15 was reported in: N. Tzvetkov, M. Schmidtmann, A. Müller, J. Mattay, Tetrahedron Lett. 2003, 44, 5979-5982.
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31144478994
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Tzvetkov, N.T.1
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31144473744
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note
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2 in THF in the presence of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)- pyrimidinone (DMPU) as an additive. The product 30 (35%) was isolated by column chromatography (cyclohexane/EtOAc, 90:10) as a colourless oil.
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-
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59
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31144464324
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note
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All calculations were carried out with Titan V1.05, Schrödinger Inc., Wavefunction Inc., 2000.
-
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61
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31144457329
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note
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For the calculations of the energy profiles of the corresponding 6-endo and 5-exo radicals we used a combination of the B3LYP level and the 6-31G* basis set. The conformational analysis and the transition states were calculated at a semiempirical level (AM1).
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64
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84914322252
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65
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31144461187
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note
-
2 afforded a mixture of the compounds 31 and 34 in 18% combined yield as well as the non-cyclized product 33 in 3% yield after chromatographic purification (cyclohexane/EtOAc 80:20). The product ratio was determined by GC as 2:1 (34:31).
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