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One-Pot Synthesis of β,β-Disubstituted α,β-Unsaturated Carbonyl Compounds

Masaharu Sugiura*, Yasuhiko Ashikari and Makoto Nakajima

*Graduate School of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Chuo-ku, Kumamoto 862-0973, Japan, Email: msugiurakumamoto-u.ac.jp

M. Sugiura, Y. Ashikari, M. Nakaijima, J. Org. Chem., 2015, 80, 8830-8835.

DOI: 10.1021/acs.joc.5b01217 (free Supporting Information)


 

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Abstract

TiCl4-promoted aldol addition followed by elimination of the titanoxy group from the Ti-aldolates affords β,β-disubstituted α,β-unsaturated carbonyl compounds. The use of additives, such as DMF, N,N,N′,N′-tetramethylethylenediamine, and pyridine, in the elimination step is important.

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Key Words

aldol condensation


ID: J42-Y2015