Isothiourea-Catalysed Asymmetric C-Acylation of Silyl Ketene Acetals

Philip A. Woods, Louis C. Morrill, Ryan A. Bragg, Andrew D. Smith

Research output: Contribution to journalArticlepeer-review

21 Citations (Scopus)

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-dihydro-pyrimidobenzothiazole-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).

Original languageEnglish
Pages (from-to)11060-11067
Number of pages8
JournalChemistry - A European Journal
Volume17
Issue number39
DOIs
Publication statusPublished - Sept 2011

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