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Synthesis of (αR,βS)-epoxyketones by asymmetric epoxidation of chalcones with cinchona phase-transfer catalysts

✍ Scribed by Mi-Sook Yoo; Dong-Guk Kim; Min Woo Ha; Sang-sup Jew; Hyeung-geun Park; Byeong-Seon Jeong

Book ID
104098233
Publisher
Elsevier Science
Year
2010
Tongue
French
Weight
382 KB
Volume
51
Category
Article
ISSN
0040-4039

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✦ Synopsis

An efficient method to synthetically produce optically enriched (aR,bS)-epoxyketones was developed using a quaternary ammonium salt derived from cinchona alkaloid as the chiral phase-transfer catalyst. (aR,bS)-Epoxyketones were prepared in high optical purities (91-99% ee) by the asymmetric epoxidation of 1,3-diarylenones with aqueous sodium hypochlorite in the presence of a hydrocinchonine-derived chiral phase-transfer catalyst bearing a 2,3,4-trifluorobenzyl group.

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Asymmetric phase-transfer mediated epoxi
Asymmetric phase-transfer mediated epoxidation of α,β-unsaturated ketones using catalysts derived from Cinchona alkaloids
✍ Barry Lygo; Philip G. Wainwright 📂 Article 📅 1998 🏛 Elsevier Science 🌐 French ⚖ 251 KB

The enantioselective epoxidation of ot,~-un~turated ketones utilising Cinchona alkaloidderived quaternary ammonium phase-transfer catalysts bearing an N-anthracenylmethyl function are presented. It has been found that the O-benzyl derivatives of these catalysts in conjunction with sodium hypochlorit