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Aza-MBH reactions are accelerated in the presence of acidic and basic catalysts. See: (a) Matsui, K.; Takizawa, S.; Sasai, H. J. Am. Chem. Soc. 2005, 127, 3680.
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33
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33645407140
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note
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2 (36% yield, 45% ee), toluene (24% yield, 56% ee), MeCN (38% yield, 48% ee), DMF (34% yield, 21% ee), MeOH (22% yield, 21% ee).
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34
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33645391499
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note
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Results of the aza-MBH reaction of 2a with 3a catalyzed by organocatalysts 1d-i in t-BuOMe (0.05 M; substrate concentration of 3a) at -20 °C for 144 h: 1d (no reaction), 1e (71% yield, 88% ee), If (80% yield, 86% ee), 1g (no reaction), 1h (14% yield, 73% ee), 1i (29% yield, 77% ee).
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35
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33645402963
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note
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13C NMR, MS, and IR spectroscopy. Absolute configurations of 5 were determined by comparing the assign of the optical rotations with those in the literature.
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-
-
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36
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33645392476
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note
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The aza-MBH reaction of 2a with 3a was performed in t-BuOMe (0.05M; substrate concentration of 3a) at 0 °C; 6a: no reaction; 6b: (S)-4a, 86 h, 5% yield, 63% ee; 6c: (R)-4a, 48 h, 95% yield, 61% ee.
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37
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0032561490
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Meng, Y.; Slaven, W. T. IV; Wang, D.; Liu, T.-J.; Chow, H.-F.; Li, C.-J. Tetrahedron: Asymmetry 1998, 9, 3693.
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0030749151
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(a) ten Have, R.; Huisman, M.; Meetsma, A.; van Leusen, A. M. Tetrahedron 1997, 53, 11355.
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0347778733
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