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For related lactol reductions, see: (a) Coghlan, M. J.; Kym, P. R.; Elmore, S. W.; Wang, A. X.; Luly, J. R.; Wilcox, D.; Stashko, M.; Lin, C.-W.; Miner, J.; Tyree, C.; Nakane, M.; Jacobson, P.; Lane, B. C. J. Med. Chem. 2001, 44, 2879-2885.
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Over-addition occurs at higher temperatures: Geissman, T. A. J. Am. Chem. Soc. 1940, 62, 1363-1367. Overreduction was also observed with PhLi in THF.
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Geissman, T.A.1
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33750379154
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note
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Heating the product mixtures did not change the ratio of products, so we assume that thermodynamic product ratios are obtained.
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12
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(a) Chamberland, S.; Ziller, J. W.; Woerpel, K. A. J. Am. Chem. Soc. 2005, 127, 5322-5323.
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33750350655
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note
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This is consistent with the known steric interaction between these two aryl groups in the atropisomeric myristinins B and C.
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21
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0035802329
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3SiH. (a) Mayr, H.; Bug, T.; Gotta, M. F.; Hering, N.; Irrgang, B.; Janker, B.; Kempf, B.; Loos, R.; Ofial, A. R.; Remennikov, G.; Schimmel, H. J. Am. Chem. Soc. 2001, 123, 9500-9512.
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