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

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

Organic letters (2011-12-14)
Blandine Ressault, Alexis Jaunet, Philippe Geoffroy, Sébastien Goudedranche, Michel Miesch
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
cis-Decahydronaphthalene, 99%
Sigma-Aldrich
trans-Decahydronaphthalene, 99%
Sigma-Aldrich
Decahydronaphthalene, mixture of cis + trans, anhydrous, ≥99%
Sigma-Aldrich
Titanium(IV) chloride solution, 1.0 M in methylene chloride
Sigma-Aldrich
Decahydronaphthalene, mixture of cis + trans, reagent grade, 98%
Sigma-Aldrich
Titanium(IV) chloride solution, 0.09 M in 20% HCl
Sigma-Aldrich
Titanium(IV) chloride, ≥99.995% trace metals basis
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Titanium tetrachloride, packaged for use in deposition systems
Sigma-Aldrich
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