487063-44-5Relevant academic research and scientific papers
Titanium tetraiodide-mediated diastereoselective iodo-aldol and Mannich reactions of γ-alkoxy-α,β-alkynyl ketone derivatives
Yashiro, Kai,Ito, Shingo,Kayaki, Shota,Sakata, Keito,Mizota, Isao,Hachiya, Iwao,Shimizu, Makoto
, p. 6875 - 6885 (2016)
The development of the stereoselective synthesis of vinyl halides plays an important role in organic chemistry. The multi-functionalized vinyl iodide is one of the most important intermediates in functional organic compounds. We investigated stereoselective iodo-aldol and iodo-Mannich reactions using γ-alkoxy-α,β-alkynyl ketones. Characteristic features of titanium tetraiodide involve iodination ability and moderate Lewis acidity, which are successfully used for the present stereoselective synthesis of multi-functionalized vinyl iodides. Furthermore, we have succeeded in the synthesis of a useful tetra-substituted furan, via a Sonogashira coupling of the vinyl iodide moiety. The factors to control diastereoselectivity of the iodo-aldol reactions are explained in terms of theoretical calculations. Consequently, the obtained activation free energy and reaction energy indicate the experimentally observed E/Z-selectivity.
