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Issue 31, 2013
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Enantioselective access to benzannulated spiroketals using a chiral sulfoxide auxiliary

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Abstract

This article describes our efforts to develop an asymmetric synthesis of bisbenzannulated spiroketals using a chiral sulfoxide auxiliary. Our primary focus was on the synthesis of the 3H-spiro[benzofuran-2,2′-chroman] ring system, the spirocyclic core of the rubromycin family. Our strategy employed the use of lithium–halogen exchange on a racemic bromospiroketal in order to attach a chiral sulfoxide, thus producing two diastereomers. The diastereomers were separable, enabling isolation of each spiroketal enantiomer. Subsequent cleavage of the sulfoxide group from each diastereomer yielded the respective parent spiroketal in high enantiopurity.

Graphical abstract: Enantioselective access to benzannulated spiroketals using a chiral sulfoxide auxiliary

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Publication details

The article was received on 22 May 2013, accepted on 18 Jun 2013 and first published on 19 Jun 2013


Article type: Paper
DOI: 10.1039/C3OB41065J
Citation: Org. Biomol. Chem., 2013,11, 5147-5155
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    Enantioselective access to benzannulated spiroketals using a chiral sulfoxide auxiliary

    H. R. M. Aitken, D. P. Furkert, J. G. Hubert, J. M. Wood and M. A. Brimble, Org. Biomol. Chem., 2013, 11, 5147
    DOI: 10.1039/C3OB41065J

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