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For recent applications of hydrazones as carbene precursors, see: (a) Aggarwal, V. K.; de Vicente, J.; Bonnert, R. V. Org. Lett. 2001, 3, 2785-2788. (b) May, J. A.; Stoltz, B. M. J. Am. Chem. Soc. 2002, 124, 12426-12427. (c) Zhang, J.-L.; Chan, P. W. H.; Che, C.-M. Tetrahedron Lett. 2003, 44, 8733-8737. (d) Aggarwal, V. K.; Winn, C. L. Acc. Chem. Res. 2004, 37, ASAP.
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For use of iodonium ylides as carbene precursors, see: (a) Müller, P.; Fernandez, D. Helv. Chim. Acta 1995, 78, 947-958. (b) Wurz, R. P.; Charette, A. B. Org. Lett. 2002, 4, 4531-4533. (c) Müller, P.; Ghanem, A. Synlett 2003, 1830-1833. (d) Wurz, R. P.; Charette, A. B. J. Org. Chem. 2004, 69, 1262-1269. (e) Müller, P. Acc. Chem. Res. 2004, 37, 243-251.
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(c) Detrifluoroacetylative diazo transfer to form α-diazo-γ- lactones has been described. See: Brown, R. C. D.; Bataille, C. J. R.; Bruton, G.; Hinks, J. D.; Swain, N. A. J. Org. Chem. 2001, 66, 6719-6728.
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Axial coordination of dirhodium catalysts by Lewis basic ligands is known to inhibit catalytic activity; see: Nagashima, T.; Davies, H. M. L. Org. Lett. 2002, 4, 1989-1992.
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For a discussion of the unique electronic properties of o-NBS A, see: Besenyei, G.; Párkányi, L.; Foch, I.; Simándi, L. I.; Kálmán, A. J. Chem. Soc., Perkin Trans. 2 2000, 1798-1802.
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4043100389
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note
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In the absence of BnOH, several decomposition products are observed, none of which appear to correspond, however, to the α,β-unsaturated lactone or dimerized material.
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20
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4 has been employed previously for X-H insertion reaction. See: Cox, G. G.; Miller, D. J.; Moody, C. J.; Sie, E.-R. H. B. Tetrahedron 1994, 50, 3195-3212.
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24
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4043164121
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note
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4 is available in Supporting Information.
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0001060227
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For select examples of intramolecular N-H insertion reactions leading to substituted prolines, see: (a) Moyer, M. P.; Feldman, P. L.; Rapoport, H. J. Org. Chem. 1985, 50, 5223-5230. (b) Davis, F. A.; Fang, T.; Goswami, R. Org. Lett. 2002, 4, 1599-1602. (c) Davis, F. A.; Yang, B.; Deng, J. J. Org. Chem. 2003, 68, 5147-5152.
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For select examples of intramolecular N-H insertion reactions leading to substituted prolines, see: (a) Moyer, M. P.; Feldman, P. L.; Rapoport, H. J. Org. Chem. 1985, 50, 5223-5230. (b) Davis, F. A.; Fang, T.; Goswami, R. Org. Lett. 2002, 4, 1599-1602. (c) Davis, F. A.; Yang, B.; Deng, J. J. Org. Chem. 2003, 68, 5147-5152.
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0038209587
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For select examples of intramolecular N-H insertion reactions leading to substituted prolines, see: (a) Moyer, M. P.; Feldman, P. L.; Rapoport, H. J. Org. Chem. 1985, 50, 5223-5230. (b) Davis, F. A.; Fang, T.; Goswami, R. Org. Lett. 2002, 4, 1599-1602. (c) Davis, F. A.; Yang, B.; Deng, J. J. Org. Chem. 2003, 68, 5147-5152.
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