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Isothiourea-catalysed asymmetric C-acylation of silyl ketene acetals |
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| Authors: | Woods Philip A Morrill Louis C Bragg Ryan A Smith Andrew D |
| Institution: | Department EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, Fife, KY16 9ST, UK. |
| Abstract: | Screening of a range of chiral isothioureas and acyl donors to promote the asymmetric C-acylation of silyl ketene acetals indicates that C(2)-aryl-dihydropyrimidobenzothiazole-derived isothioureas and propionic anhydride give optimal reactivity and enantioselectivity in this process. Under optimised conditions 3-acyl-3-aryl or 3-acyl-3-alkylfuranones are prepared in good yields and moderate to excellent enantioselectivities (up to 98% ee; ee=enantiomeric excess). |
| Keywords: | acylation asymmetric synthesis isothioureas organocatalysis silyl ketene acetals |
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