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Volumn 6, Issue 4, 2004, Pages 641-644

Oxazolidine Ring Opening and Isomerization to (E)-Imines. Asymmetric Synthesis of Aryl-α-fluoroalkyl Amino Alcohols

Author keywords

[No Author keywords available]

Indexed keywords

AMINOALCOHOL; IMINE; ORGANOMETALLIC COMPOUND; OXAZOLIDINE DERIVATIVE;

EID: 1342268976     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol036486g     Document Type: Article
Times cited : (51)

References (25)
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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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    • (1991) Tetrahedron Lett. , vol.32 , pp. 987-990
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    • For reviews on organometallic additions to imines and their derivatives see: Bloch, R. Chem. Rev. 1998, 98, 1407-1438. Enders, D.; Reinhold: U. Tetrahedron: Asymmetry 1997, 8, 1895-1946.
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    • For reviews on organometallic additions to imines and their derivatives see: Bloch, R. Chem. Rev. 1998, 98, 1407-1438. Enders, D.; Reinhold: U. Tetrahedron: Asymmetry 1997, 8, 1895-1946.
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    • note
    • 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.
  • 21
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    • note
    • 1H NMR spectroscopic analysis confirmed that imine 4 was a single geometric isomer.
  • 23
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    • note
    • 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.
  • 24
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    • note
    • 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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