Issue 31, 2013

Enantioselective access to benzannulated spiroketals using a chiral sulfoxide auxiliary

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

Supplementary files

Article information

Article type
Paper
Submitted
22 May 2013
Accepted
18 Jun 2013
First published
19 Jun 2013

Org. Biomol. Chem., 2013,11, 5147-5155

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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