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Volumn 54, Issue 42, 1998, Pages 12789-12806

Chiral sulfoxide controlled asymmetric additions to C-N double bond. An efficient approach to stereochemically defined α-fluoroalkyl amino compounds

Author keywords

[No Author keywords available]

Indexed keywords

ALIPHATIC AMINE; SULFOXIDE;

EID: 0032532260     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00779-0     Document Type: Article
Times cited : (84)

References (91)
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    • ref. 3 (b).
    • 4 For discussion on stereochemical properties of fluorine substituents see: (a) ref. 3 (b).
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    • 9 For reviews see: (a) Posner, G. H. In The Chemistry of Sulphones and Sulphoxides; Patai, S.; Rappoport, Z.; Stirling, C. J. M., Eds.; Wiley: New York, 1988.
    • (1988) The Chemistry of Sulphones and Sulphoxides
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    • 15 PMP-group is known as versatile protecting group, and in most cases, could be subsequently removed to afford a free amino function; Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; Wiley: London, 1991.
    • (1991) Protective Groups in Organic Synthesis
    • Greene, T.W.1    Wuts, P.G.M.2
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    • For a discussion on the configurational stability of imino compounds see: (c) Lefebvre, I. M.; Evans, S. A., Jr. J. Org. Chem. 1997, 62, 7532 and references therein.
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    • note
    • 17 On the other hand, this beneficial property of 7a-c could create some problems in determining the stereochemical outcome of small scale reactions, as it was in our initial study. Thus, the diastereomeric ratios reported in the preliminary communication (ref. 13) should be corrected.
  • 73
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    • note
    • 18 In the original text of ref. 12c compound Et-CH=N-Ph is named as N-ethylideneaniline.
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    • note
    • S,1R*,2R*).
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    • See ref. 9d.
    • 20 (a) See ref. 9d.
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    • 21 For Curtin-Hammett principle, which states that for some reactions the thermodynamically preferred and reactive geometries are not identical, see: (a) Seeman, J. I. Chem. Rev. 1983, 83, 83.
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    • note
    • S)-7a through chiral HPLC analysis (N-2,3-dinitrobenzoyl derivatives) unequivocally confirmed that the samples are homochiral [(R)-absolute configuration].


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