Access to polyfunctionalized diquinanes, hydrindanes, and decalines via TiCl4 promoted Michael-aldol and Baylis-Hillman reactions.

Blandine Ressault, Alexis Jaunet, Philippe Geoffroy, Sébastien Goudedranche, Michel Miesch

Index: Org. Lett. 14(1) , 366-9, (2012)

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Abstract

The addition of 0.5 equiv of TiCl(4) to (cyclo)alkanones tethered to α,β-unsaturated ketones afforded polyfunctionalized diquinanes, hydrindanes, and decalines. These products, resulting from a Michael-aldol or a Baylis-Hillman reaction, can be obtained with high or total diastereoselectivity in moderate to high yields. These scaffolds represent interesting building blocks for the synthesis of complex natural products.© 2011 American Chemical Society