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For reviews on the biological significance of organofluorine compounds see: (a) Resnati, G., Soloshonok, V. A., Eds.; Tetrahedron Symposia-in-Print No 58; Fluoroorganic Chemistry: Synthetic Challenges and Biomedical Rewards. Tetrahedron 1996, 52, 1-330. (b) Fluorine Containing Amino Acids: Synthesis and Properties; Kuhar, V. P., Soloshonok, V. A. Eds.; Wiley: Chichester, UK, 1994. (c) Biomedicinal Aspects of Fluorine Chemistry, Filler, R., Kobayashi, Y., Yagupolskii, L. M., Eds.; Elsevier: Amsterdam, The Netherlands, 1993.
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For reviews on the biological significance of organofluorine compounds see: (a) Resnati, G., Soloshonok, V. A., Eds.; Tetrahedron Symposia-in-Print No 58; Fluoroorganic Chemistry: Synthetic Challenges and Biomedical Rewards. Tetrahedron 1996, 52, 1-330. (b) Fluorine Containing Amino Acids: Synthesis and Properties; Kuhar, V. P., Soloshonok, V. A. Eds.; Wiley: Chichester, UK, 1994. (c) Biomedicinal Aspects of Fluorine Chemistry, Filler, R., Kobayashi, Y., Yagupolskii, L. M., Eds.; Elsevier: Amsterdam, The Netherlands, 1993.
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Asymmetric syntheses of perfluoroalkylamines include the following: (a) Surya Prakash, G. K.; Mandal, M.; Olah, G. A. Angew. Chem., Int. Ed. 2001, 40, 589-590. (b) Surya Prakash, G. K.; Mandal, M.; Olah, G. A. Org. Lett. 2001, 3, 2847-2850. (c) Enders, D.; Funabiki, K. Org. Lett. 2001, 3, 1575-1577. (d) Soloshonok, V. A.; Ono, T. J. Org. Chem. 1997, 62, 3030-3031. (e) Ishii, A.; Higashiyama, K.; Mikami, K. Synlett 1997, 1381-1382. (f) Wang, Y.; Mosher, H. S. Tetrahedron Lett. 1991, 32, 987-990. (g) Pirkle, W. H.; Hauske, J. R. J. Org. Chem. 1977, 42, 2436-2439.
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Asymmetric syntheses of perfluoroalkylamines include the following: (a) Surya Prakash, G. K.; Mandal, M.; Olah, G. A. Angew. Chem., Int. Ed. 2001, 40, 589-590. (b) Surya Prakash, G. K.; Mandal, M.; Olah, G. A. Org. Lett. 2001, 3, 2847-2850. (c) Enders, D.; Funabiki, K. Org. Lett. 2001, 3, 1575-1577. (d) Soloshonok, V. A.; Ono, T. J. Org. Chem. 1997, 62, 3030-3031. (e) Ishii, A.; Higashiyama, K.; Mikami, K. Synlett 1997, 1381-1382. (f) Wang, Y.; Mosher, H. S. Tetrahedron Lett. 1991, 32, 987-990. (g) Pirkle, W. H.; Hauske, J. R. J. Org. Chem. 1977, 42, 2436-2439.
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Asymmetric syntheses of perfluoroalkylamines include the following: (a) Surya Prakash, G. K.; Mandal, M.; Olah, G. A. Angew. Chem., Int. Ed. 2001, 40, 589-590. (b) Surya Prakash, G. K.; Mandal, M.; Olah, G. A. Org. Lett. 2001, 3, 2847-2850. (c) Enders, D.; Funabiki, K. Org. Lett. 2001, 3, 1575-1577. (d) Soloshonok, V. A.; Ono, T. J. Org. Chem. 1997, 62, 3030-3031. (e) Ishii, A.; Higashiyama, K.; Mikami, K. Synlett 1997, 1381-1382. (f) Wang, Y.; Mosher, H. S. Tetrahedron Lett. 1991, 32, 987-990. (g) Pirkle, W. H.; Hauske, J. R. J. Org. Chem. 1977, 42, 2436-2439.
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Asymmetric syntheses of perfluoroalkylamines include the following: (a) Surya Prakash, G. K.; Mandal, M.; Olah, G. A. Angew. Chem., Int. Ed. 2001, 40, 589-590. (b) Surya Prakash, G. K.; Mandal, M.; Olah, G. A. Org. Lett. 2001, 3, 2847-2850. (c) Enders, D.; Funabiki, K. Org. Lett. 2001, 3, 1575-1577. (d) Soloshonok, V. A.; Ono, T. J. Org. Chem. 1997, 62, 3030-3031. (e) Ishii, A.; Higashiyama, K.; Mikami, K. Synlett 1997, 1381-1382. (f) Wang, Y.; Mosher, H. S. Tetrahedron Lett. 1991, 32, 987-990. (g) Pirkle, W. H.; Hauske, J. R. J. Org. Chem. 1977, 42, 2436-2439.
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Asymmetric syntheses of perfluoroalkylamines include the following: (a) Surya Prakash, G. K.; Mandal, M.; Olah, G. A. Angew. Chem., Int. Ed. 2001, 40, 589-590. (b) Surya Prakash, G. K.; Mandal, M.; Olah, G. A. Org. Lett. 2001, 3, 2847-2850. (c) Enders, D.; Funabiki, K. Org. Lett. 2001, 3, 1575-1577. (d) Soloshonok, V. A.; Ono, T. J. Org. Chem. 1997, 62, 3030-3031. (e) Ishii, A.; Higashiyama, K.; Mikami, K. Synlett 1997, 1381-1382. (f) Wang, Y.; Mosher, H. S. Tetrahedron Lett. 1991, 32, 987-990. (g) Pirkle, W. H.; Hauske, J. R. J. Org. Chem. 1977, 42, 2436-2439.
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1342284589
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note
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See ref 3e. As noted by these authors, chromatographic separation of diastereoisomers of (R)-phenylglycinol-derived 2-trifluoromethyl-1, 3-oxazolidine prior to organometallic addition was required to obtain adducts with diastereomeric ratios up to ∼8:1.
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1342327093
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note
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1H NMR spectroscopic analysis confirmed that imine 4 was a single geometric isomer.
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0037178513
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During the course of our work, a conceptually related method for opening acetals and oxazolidines was reported: Iwata, A.; Tang, H.; Kunai, A.; Ohshita, J.; Yamamoto, Y.; Matui, C. J. Org. Chem. 2002, 67, 5170-5175.
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Iwata, A.1
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23
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1342284588
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note
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The minor diastereomer was quantified by HPLC, using enriched samples prepared by direct organolithium addition to oxazolidines 2a-g that typically gave ℱ2:1 diastereomeric ratios.
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24
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1342284587
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note
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Solutions of aryllithium species were freshly generated from the corresponding aryl bromides via halogen-metal exchange with n-BuLi or by deprotonation of the corresponding hydrocarbon in the case of furan.
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