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Isothiourea‐Catalysed Asymmetric C ‐Acylation of Silyl Ketene Acetals
Author(s) -
Woods Philip A.,
Morrill Louis C.,
Bragg Ryan A.,
Smith Andrew D.
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201100995
Subject(s) - ketene , acylation , chemistry , silylation , aryl , enantiomer , reactivity (psychology) , enantiomeric excess , medicinal chemistry , enantioselective synthesis , organic chemistry , catalysis , medicine , alkyl , alternative medicine , pathology
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).