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Letters in Organic Chemistry

Author(s): Narayan V. Mayekar, Subrata Chattopadhyay and Sandip K. Nayak

DOI: 10.2174/1570178043400857

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Influence of the Nature of Low Valent Titanium Reagents in McMurry Olefination: Stereoselective Synthesis of Symmetrical and Unsymmetrical Hydroxystilbenes

Page: [203 - 207] Pages: 5

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Abstract

Intramolecular reductive deoxygenation of ethylenedioxy tethered symmetrical and unsymmetrical aromatic bis(ketone) ethers with the low-valent titanium (LVT) reagent (TiCl4-Zn-DME) yielded the corresponding cyclic stilbenes with excellent Z-selectivity. On the other hand, coupling of the aldehydic tethered ethers proceeded with high E-selectivity with the LVT reagent (TiCl3 / Li / KCl (2.0 eq.) / THF). Dealkylation of the cyclic stilbenes furnished the geometrically pure hydroxystilbenes.

Keywords: hydroxystilbenes, low-valent titanium (lvt) reagents, mcmurry coupling, stereocontrolled reaction