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Development of β-keto 1,3-dithianes as versatile intermediates for organic synthesis

Matthew J. Gaunt , Helen F. Sneddon , Peter R. Hewitt , Paolo Orsini , David F. Hook and Steven V. Ley*

*University Chemical Laboratory, Lensfield Road, Cambridge, UK CB2 1 EW, Email: svl1000cam.ac.uk

M. J. Gaunt, H. F. Sneddon, P. R. Hewitt, P. Orsini, D. F. Hook, S. V. Ley, Org. Biomol. Chem., 2003, 1, 15-16.

DOI: 10.1039/b208982c


Abstract

β-Keto 1,3-dithianes can be generated by the double conjugate addition of dithiols to propargylic ketones, esters and aldehydes in excellent yields. These masked 1,3-dicarbonyl systems can be converted to a range of functionalised oxygen-containing heterocycles that can be used in natural product synthesis.

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proposed mechanism



Key Words

1,3-dithianes, conjugate addition


ID: J52-Y2003-1140