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Synthesis 2001; 2001(4): 0577-0580
DOI: 10.1055/s-2001-12359
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1,2-Epimino-3,4-epoxybutane: A Versatile Chiral Building Block

Guido Harms* , Ernst Schaumann, Gunadi Adiwidjaja
  • *Institut für Organische Chemie, Technische Universität Clausthal, Leibnizstraße 6, 38678 Clausthal-Zellerfeld, Germany; Fax + 49(53 23)72 28 58; E-mail: ernst.schaumann@tu-clausthal.de
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Publication Date:
31 December 2001 (online)

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The synthesis of enantiomerically pure 1,2-epimino-3,4-epoxy-(N-toluenesulfonyl)butane (6) in the S,R-(erythro) and R,R-(threo) configurations is described. This building block offers a new route to targets with an 1,2-aminohydroxy functionality. As an example, the new 1,4-biselectrophile is employed in a cyclopentane synthesis.

amino alcohols - domino reactions - epoxides - ring opening - cyclopentanes

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