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c)For a dynamic kinetic resolution, see: Z. Zhang, C. F. Bender, R. A. Widenhoefer, J. Am. Chem. Soc. 2007, 129, 14148-14149;
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For a previous report of asymmetric hydroamination of (maximum ee value was 16%)
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For an gold(I)-catalyzed asymmetric hydroalkoxylation of allenes
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e) For an gold(I)-catalyzed asymmetric hydroalkoxylation of allenes, see: Z. Zhang, R. A. Widenhoefer, Angew. Chem. 2007, 119, 287-289;
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For a review of recent developments in enantioselective gold catalysis
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For a racemic gold-catalyzed synthesis of N-hydroxypyrrolines, dihydroisoxazoles, and dihydro-l,2-oxazines
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For a racemic gold-catalyzed synthesis of N-hydroxypyrrolines, dihydroisoxazoles, and dihydro-l,2-oxazines, see: a) C. Winter, N. Krause, Angew. Chem. 2009, 121, 6457-6460;
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For a gold(I)-catalyzed addition of hydroxylamines to alkynes
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For a gold(I)-catalyzed addition of hydroxylamines to alkynes, see: b)H.-S. Yeom, E.-S. Lee, S. Shin, Synlett 2007, 2292-2294;
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For a single example of an intermolecular gold(I)-catalyzed addition of methyl carbamate to tetramethyl allene (61 % yield)
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For a single example of an intermolecular gold(I)-catalyzed addition of methyl carbamate to tetramethyl allene (61 % yield), see: a) R. E. Kinder, Z. Zhang, R. A. Widenhoefer, Org. Lett. 2008, 10, 3157-3159;
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For a single example of an intermolecular gold(I)-catalyzed addition of indole to tetramethyl allene (56% yield)
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For a single example of an intermolecular gold(I)-catalyzed addition of indole to tetramethyl allene (56% yield), see: b) K. Toups, G. Liu, R. A. Widenhoefer, J. Organomet. Chem. 2009, 694, 571-575.
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2], 6mol% (S)-Ag(5), 0.1M in toluene, 23 °C, 18 h gave oxazine 27 in 60% yield and 34% ee
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2], 6mol% (S)-Ag(5), 0.1M in toluene, 23 °C, 18 h gave oxazine 27 in 60% yield and 34% ee.
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The absolute configuration of U was assigned by oxidative cleavage, Boc removal, and Cbz protection to (S)-methyl-2benzyloxycarbonyl-3- isoxazolidinecarboxylate (see the Supporting Information). The absolute configurations of the remaining hydroamination products were assigned by analogy to 11
-
The absolute configuration of U was assigned by oxidative cleavage, Boc removal, and Cbz protection to (S)-methyl-2benzyloxycarbonyl-3- isoxazolidinecarboxylate (see the Supporting Information). The absolute configurations of the remaining hydroamination products were assigned by analogy to 11.
-
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44
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For a representative procedure to cleave the N-O bond
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