Synthesis of Derivatives of (1R)-(-)- and (1S)-(+)-10-Camphorsulfonic Acid

Steven C. Cermak and David F. Wiemer
Department of Chemistry, University of Iowa, Iowa City, IA 52242
J. Chem. Educ., 1999, 76 (12), p 1715
DOI: 10.1021/ed076p1715
Publication Date (Web): December 1, 1999

Abstract

The preparation of optically active (camphorsulfonyl)oxaziridines from commercially available (1R)-(-) and/or (1S)-(+)10-camphorsulfonic acid provides a clear demonstration of the lack of relationship between absolute configuration and optical rotation. The parent sulfonic acid can be converted to the corresponding acid chloride and then to the sulfonamide, sulfonylimine, and finally to an oxaziridine in a series of practical organic laboratory experiments. The absolute configuration remains the same through this series of transformations, but the sign of the optical rotation is reversed from the sulfonamide to the sulfonylimine, and again from the sulfonylimine to the oxaziridine. The latter two intermediates are readily purified by crystallization, and their optical rotations are easily measured.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Organic Chemistry

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Stereochemistry

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This article has been cited by 1 ACS Journal articles (1 most recent appear below).

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    Microscale Synthesis of Chiral Alcohols via Asymmetric Catalytic Transfer Hydrogenation

    Dirk De Vos , Christine M. Peeters and Rik Deliever
    Journal of Chemical Education2009 86 (1), 87
    • Microscale Synthesis of Chiral Alcohols via Asymmetric Catalytic Transfer Hydrogenation

      Dirk De Vos , Christine M. Peeters and Rik Deliever
      Journal of Chemical Education2009 86 (1), 87

      Synthesis of pure enantiomers is a key issue in industry, especially in areas connected to life sciences. Catalytic asymmetric synthesis has emerged as a powerful and practical tool. Here we describe an experiment on racemic reduction and asymmetric ...

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History

  • Received: August 03, 2009

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