ol203118t_si_009.cif (14.25 kB)

Access to Polyfunctionalized Diquinanes, Hydrindanes, and Decalines via TiCl4 Promoted Michael–Aldol and Baylis–Hillman Reactions

Download (14.25 kB)
posted on 06.01.2012 by Blandine Ressault, Alexis Jaunet, Philippe Geoffroy, Sébastien Goudedranche, Michel Miesch
The addition of 0.5 equiv of TiCl4 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.