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α,α′-Dioxothiones part 2. Asymmetric Diels-Alder reactions of chiral non-racemic α,α′-dioxothiones

✍ Scribed by Giorgio Boccardo; Giuseppe Capozzi; Meri Giuntini; Stefano Menichetti; Cristina Nativi

Book ID: 104208225
Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 660 KB
Volume: 53
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(97)10162-4

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✦ Synopsis

Chiral non-racemic ¢x,ct'-dioxothiones 2a.g and 17 are obtained from chiral [~-ketoesters using the phthalimidesulfenyl chloride 1 as key reagent. The ability of these thiones to discriminate between the enantiotopic faces of several dienophiles has been evaluated. The best diastereoisomeric excesses (67-80%) were obtained when the ct-acyl thiones were involved as electron-poor dienes in inverse electron demand Diets-Alder reactions with electron-rich styrenes as dienophiles. The possibility to obtain thiones bearing two chiral groups as well as the reactions where the ct-acyl thiones 2 participate as dienophiles are also shown.

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