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Asymmetric synthesis of α,β-epoxysulfones under phase-transfer catalyzed Darzens reaction

✍ Scribed by Shigeru Arai; Toshimasa Ishida; Takayuki Shioiri

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
235 KB
Volume
39
Category
Article
ISSN
0040-4039

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✦ Synopsis

Enantioselective synthesis of ct, l~-epoxysulfones by the Darzens reaction was achieved under phase-transfer catalyzed conditions. The reaction of chloromethyl phenylsulfone with various aromatic aldehydes smoothly proceeded in the presence of a catalytic amount (10 mol %) of chiral quaternary ammonium salt derived from quinine with KOH at room temperature to afford the desired coupling products in good yield with up to 81% ee.

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Asymmetric alkylation reaction of α-fluorotetralone under phase-transfer catalyzed conditions
✍ Shigeru Arai; Makoto Oku; Toshimasa Ishida; Takayuki Shioiri 📂 Article 📅 1999 🏛 Elsevier Science 🌐 French ⚖ 267 KB

The catalytic asymmetric alkylation reaction of 0t-fluorotetralones promoted by a chiral quaternary ammonium salt derived from cinchonine under phase-transfer catalyzed conditions was described. The reaction proceeded smoothly to give the desired products with up to 91% ee. This methodology provides