• Substitution with retention in organoboranes and utilization of the phenomenon for a general synthesis of pure enantiomers

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    • Keywords


      Substitution with retention; organoboranes; synthesis of pure enantiomers; retention of stereochemistry

    • Abstract


      Organoboranes, readily available via the hydroboration of unsaturated organic compounds, exhibit a remarkable versatility in their reactions. The boron atom in these organoboranes can be readily converted into a wide variety of organic groups under very mild conditions, providing simple versatile syntheses of organic compounds. Exploration of these substitution reactions reveal that, with rare exceptions, the organoboranes transfer the alkyl group to other elements of synthetic interest with complete retention of stereochemistry. Recently we have discovered a method of synthesizing essentially optically pure organoborane intermediates. These optically active alkyl groups attached to boron can also be transferred with complete retention of optical activity. Consequently, it is now possible to achieve by a rational synthesis the preparation of almost any optically active compound with a chiral center, either R- or S-, in essentially 100% enantiomeric excess.

    • Author Affiliations


      Herbert C Brown1 Bakthan Singaram1

      1. H C Brown and R B Wetherill Laboratories of Chemistry, Purdue University, West Lafayette, Indiana - 47907, USA
    • Dates

  • Journal of Chemical Sciences | News

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