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Synthesis 1996; 1996(3): 367-371
DOI: 10.1055/s-1996-4208
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Synthesis of 2,4,5-Triphenyl-Substituted Oxazolidine and 2,5-Diphenyl-Substituted Pyrrolidine Derivatives

Claudia Wittland, Michael Arend, Nikolaus Risch*
  • *Universität-GH Paderborn, Fachbereich für Chemie und Chemietechnik, Warburger Str. 100, D-33098 Paderborn, Germany
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Publication Date:
31 December 2000 (online)

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A simple one-pot domino reaction procedure for the stereoselective synthesis of oxazolidines and C 2-symmetric pyrrolidines from inexpensive starting materials is described. Azomethine ylides generated in situ by heating a mixture of benzaldehyde and benzylic amines are trapped with dipolarophiles by a 1,3-dipolar cycloaddition reaction. The products represent valuable synthetic building blocks or potential starting materials for the preparation of chiral auxiliaries and are difficult to obtain by other methods.

azomethine ylides - 1,3-dipolar cycloadditions - oxazolidines - pyrrolidines - C2-symmetrical auxiliaries

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