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although trichloromethyl carbinols were oxidized mainly by using stoichiometric amounts of chromium(VI) reagents in the original report, we utilized the catalytic oxidation method reported by workers at Merck: b) M. Zhao, J. Li, Z. Song, R. Desmond, D. M. Tschaen, E. J. J. Grabowski, P. J. Reider, Tetrahedron Lett. 1998, 39, 5323; Swern oxidation is also applicable, see Supporting Information.
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33746204734
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note
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2} (10 mol%), also promoted the Mannich reaction of imine 2d with 1a (5 equiv) at -40°C in comparable yield (conv. 89%), albeit with lower syn selectivity (syn/anti = 13:1) and longer reaction time (13h) than the corresponding reactions in Table 1.
-
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55
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20344364640
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The N-Dpp group is useful because it is readily removed; for a review on the use of N-Dpp imines in organic synthesis, see: S. M. Weinreb, R. K. Orr, Synthesis 2005, 1205.
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33746204733
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note
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[22] the relative configurations of 3da and 3la were determined after conversion into known compounds; see Supporting Information.
-
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60
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33746235135
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Wiley, New York, chap. 9, see also reference [11c]
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For discussions on steric effects of the trichloromethyl group, see: M. B. Smith, J. March, Advanced Organic Chemistry, 5th ed., Wiley, New York, 2001, chap. 9, p. 374; see also reference [11c].
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33746187598
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note
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The relative configuration of 8da was determined by X-ray crystallographic analysis of the corresponding cyclic carbamate; see Supporting Information.
-
-
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62
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33746187597
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-
note
-
For the determination of the relative configurations of 10da and 12da, see Supporting Information.
-
-
-
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63
-
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33746204732
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CCDC 295183-295185 (12da, 3fa, cyclic carbamate derived from 8da, respectively) contain 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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