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For related asymmetric reductive aldol reactions, see: (a) Taylor, S. J.; Duffey, M. O.; Morken, J. P. J. Am. Chem. Soc. 2000, 122, 4528-4529.
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84872277981
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note
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Fast Red TR salt (4-chloro-2-methylbenzenediazonium chloride) is commercially available from Aldrich Chemical Co.
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24
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The PMP group is readily removed from the β-lactam nitrogen under CAN oxidation conditions, see: (a) Georg, G. I.; Kant, J.; Gill, H. S. J. Am. Chem. Soc. 1987, 109, 1129-1135.
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(b) Ojima, I.; Habus, I.; Zhao, M.; Zucco, M.; Park, Y. H.; Sun, C. M.; Brigaud, T. Tetrahedron 1992, 48, 6985-7012.
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Addition of an Ir(I) hydride to methyl acrylate in the presence of dioxygen is proposed to provide a C-bound iridium enolate. See: Droiun, M.; Harrod, J. F. Can. J. Chem. 1985, 63, 353-360.
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For addition of Pd enolates to imines, see: Fujii, A.; Hagiwara, E.; Sodeoka, M. J. Am. Chem. Soc. 1999, 121, 5450-5458. Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474-2475.
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For addition of Pd enolates to imines, see: Fujii, A.; Hagiwara, E.; Sodeoka, M. J. Am. Chem. Soc. 1999, 121, 5450-5458. Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474-2475.
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Lithium enolates of aryl esters eliminate to ketene upon warming to room temperature. See: Seebach, D.; Amstutz, R.; Laube, T.; Schweizer, W. B.; Dunitz, J. D. J. Am. Chem. Soc. 1985, 107, 5403-5409. The reverse reaction with addition of a Pd-alkoxide to ketene is postulated in a review article. See: Geoffroy, G. L.; Bassner, S. L. In Advances in Organometallic Chemistry; Stone, F. G. A., West, R., Eds.; Academic Press: San Diego, 1993; Vol. 28, p 6.
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Stone, F. G. A., West, R., Eds.; Academic Press: San Diego
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Lithium enolates of aryl esters eliminate to ketene upon warming to room temperature. See: Seebach, D.; Amstutz, R.; Laube, T.; Schweizer, W. B.; Dunitz, J. D. J. Am. Chem. Soc. 1985, 107, 5403-5409. The reverse reaction with addition of a Pd-alkoxide to ketene is postulated in a review article. See: Geoffroy, G. L.; Bassner, S. L. In Advances in Organometallic Chemistry; Stone, F. G. A., West, R., Eds.; Academic Press: San Diego, 1993; Vol. 28, p 6.
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Geoffroy, G.L.1
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[2 + 2] cycloaddition of imine 1 and methyl ketene is reported to give only the trans stereoisomer when the ketene is generated from pyrolysis of 2-butanone. See: Tschamber, T.; Streith, J. Tetrahedron Lett. 1980, 21, 4503-4506.
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note
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[2 + 2] ketene-imine cycloaddition is proposed to proceed through a zwiterionic iminium ion generated by nucleophilic addition of the imine to ketene. For a review, see: ref 1b, pp 295-368.
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