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Compound 5 is commercially available from International Laboratory
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Compound 5 is commercially available from International Laboratory, Interchim, and WaterstoneTech.
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Interchim, and WaterstoneTech
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In the original literature in ref 11, the Newman-Kwart rearrangement of 3 to 4 was examined at 285-400°C. Moreover, during the preparation of this manuscript, a 1-400 kg-scale synthesis of aryl S-thiocarbamates from aryl O-thiocarbamates in microwave reactors was reported by Moseley and co-workers. The industrial synthesis of 1 should be a great advantage. (a) Moseley, J. D.; Lenden, P.; Lockwood, M.; Ruda, K.; Sherlock, J.-P.; Thomson, A. D.; Gilday, J. P. Org. Process Res. Dev. 2008, 12, 30.
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In the original literature in ref 11, the Newman-Kwart rearrangement of 3 to 4 was examined at 285-400°C. Moreover, during the preparation of this manuscript, a 1-400 kg-scale synthesis of aryl S-thiocarbamates from aryl O-thiocarbamates in microwave reactors was reported by Moseley and co-workers. The industrial synthesis of 1 should be a great advantage. (a) Moseley, J. D.; Lenden, P.; Lockwood, M.; Ruda, K.; Sherlock, J.-P.; Thomson, A. D.; Gilday, J. P. Org. Process Res. Dev. 2008, 12, 30.
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3,3′-Bis[4-(β-naphthyl)phenyl]-substituted chiral binaphthol phosphoric acid catalyst, which was proved to be the most effective in direct Mannich-type reaction by Terada and co-workers, was prepared from (R)-BINOL in 31% over seven steps. See ref 7. Also see; Wipf, P, Jung, J.-K. J. Org. Chem. 2000, 65, 6319
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3,3′-Bis[4-(β-naphthyl)phenyl]-substituted chiral binaphthol phosphoric acid catalyst, which was proved to be the most effective in direct Mannich-type reaction by Terada and co-workers, was prepared from (R)-BINOL in 31% over seven steps. See ref 7. Also see; Wipf, P.; Jung, J.-K. J. Org. Chem. 2000, 65, 6319.
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To understand the character of our catalysts, we also examined some reactions by using the Terada's chiral phosphoric acid catalyst. See the Supporting Information in detail.
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To understand the character of our catalysts, we also examined some reactions by using the Terada's chiral phosphoric acid catalyst. See the Supporting Information in detail.
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2 even if there is a large amount of 2 relative to 1 (see eq 1 and Table 2).
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2 even if there is a large amount of 2 relative to 1 (see eq 1 and Table 2).
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71
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1,1′-Binaphthyl-2,2′-dicarboxylic acid-22 (5 mol , showed low catalytic activity and low enantioselectivity (<10% ee) in the reactions in Table 3, Scheme 3, and eq 2. Also see ref 6j
-
2 (5 mol %) showed low catalytic activity and low enantioselectivity (<10% ee) in the reactions in Table 3, Scheme 3, and eq 2. Also see ref 6j.
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