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

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posted on 06.01.2012, 00:00 authored 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.