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For the use of a catalytic urea ligand and a stoichiometric amount of metal, see:. Hernández-Rodríguez M., Gabriela Avila-Ortiz C., del Campo J.M., Hernández-Romero D., Rosales-Hoz M.J., and Juaristi E. Aust. J. Chem. 61 (2008) 364
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For examples of asymmetric Diels-Alder reactions using ketone-derived siloxy dienes, see:. Huang Y., Iwama T., and Rawal V.H. J. Am. Chem. Soc. 122 (2000) 7843
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See also:. Yamatsugu K., Yin L., Kamijo S., Kimura Y., Kanai M., and Shibasaki M. Angew. Chem., Int. Ed. 48 (2009) 1070
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Asymmetric hetero-Diels-Alder reactions are well known. Jørgensen K.A. Angew. Chem., Int. Ed. 39 (2000) 3558
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For aldehydes and ketones, see a review:
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For aldehydes and ketones, see a review:. Pellissier H. Tetrahedron 65 (2009) 2839
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Tetrahedron
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See also Ref. 10. By the addition of tertiary amine, DA adducts can be isolated as 4, and the excess diene remained unchanged during the reaction as well. Without amines, DA adducts were directly converted to 5
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Nishida A., Yamanaka M., and Nakagawa M. Tetrahedron Lett. 40 (1999) 1555 See also Ref. 10. By the addition of tertiary amine, DA adducts can be isolated as 4, and the excess diene remained unchanged during the reaction as well. Without amines, DA adducts were directly converted to 5
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Nishida, A.1
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We did not obtain reproducible results regarding the optical resolution of 6 following the reported method:
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We did not obtain reproducible results regarding the optical resolution of 6 following the reported method:. Dethloff W., and Mix H. Chem. Ber. (1949) 534
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(1949)
Chem. Ber.
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Dethloff, W.1
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0037123608
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A similar problem has been reported previously:
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A similar problem has been reported previously:. Gillespie K.M., Sanders C.J., O'Shaughnessy P., Westmoreland I., Thickitt C.P., and Scott P. J. Org. Chem. 67 (2002) 3450
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For the synthesis of racemic 6, see Ref. 15. See also:
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For the synthesis of racemic 6, see Ref. 15. See also:. Marxen T.L., Johnson B.J., Nilsson P.V., and Pignolet L.H. Inorg. Chem. 23 (1984) 4663
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note
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Recently, both isomers of optically active 6,6′-dimethyl-2,2′-biphenyldiamine (6) have become commercially available from Aldrich. The absolute configuration of 9 synthesized from (±)-6 was determined by comparison to the spectral data of 9 synthesized from purchased optically pure 6.
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For these optimized conditions with (S)-10a (10 mol %): 7% yield; -76% ee. (S)-10a was still mismatched ligand.
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Without this operation, we did not obtain reproducible results. A precise mechanistic investigation is now underway.
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For the reaction of 2a and 3a, (R)-10c has similar reactivity and selectivity to (R)-10a. But, for 2a and 3h, (R)-10c gave only 12% yield and 84% ee (0.6 M, 0 °C, 3 h).
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