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4-mediated aldol reaction of (S)-1-hydroxy-2-methyl-3-pentanone with isobutyraldehyde produces 2,4-syn-4,5-syn aldol in 92% yield and 88:12 diastereoselectivity. See: Luke, G. P.; Morris, J. J. Org. Chem. 1995, 80, 3013-3019.
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note
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Ketones 1-3 were prepared following reported procedures. See refs 7b and 7e.
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33544459538
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For recent aldol reactions involving α-hydroxy aldehydes, see: (a) Reference 10b
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For recent aldol reactions involving α-hydroxy aldehydes, see: (a) Reference 10b.
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41
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0037541165
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(b) Evans, D. A.; Siska, S. J.; Gee, V. J. Angew. Chem., Int. Ed. 2003, 42, 1761-1765.
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0026097004
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Actually, stereochemistry of aldol 11 has been secured through conversion into an advanced intermediate reported for the synthesis of erythronolides: (a) Mulzer, J.; Kirstein, H. M.; Buschmann, J.; Lehmann, C.; Luger, P. J. Am. Chem. Soc. 1991, 113, 910-923.
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