81112-82-5Relevant articles and documents
Chiral quaternary ammonium aryloxide/N,O-bis(trimethyl-silyl)acetamide combination as efficient organocatalytic system for the direct vinylogous aldol reaction of (5H)-furan-2-one derivatives
Claraz, Aurelie,Oudeyer, Sylvain,Levacher, Vincent
supporting information, p. 841 - 846 (2013/05/09)
A chiral quaternary ammonium amide was generated in situ from N,O-bis(trimethylsilyl)acetamide (BSA) as non-nucleophilic Bronsted base precursor and the combination of chiral quaternary ammonium halide/sodium aryloxide as chiral Lewis base. This system was applied to an anti-selective organocatalytic direct vinylogous aldol (ODVA) reaction of (5H)-furan-2-one derivatives with aldehydes. Several 5-(1′-hydroxy)-γ-butenolides were obtained in good diastereomeric ratios (up to 95/5) and excellent enantioselectivities (up to 94%) with both aliphatic or (hetero)aromatic aldehydes, so providing a rare example of general and efficient conditions for the ODVA reaction. Copyright
Synthesis of (+)-L-733,060, (+)-CP-99,994 and (2S,3R)-3-hydroxypipecolic acid: Application of an organocatalytic direct vinylogous aldol reaction
Pansare, Sunil V.,Paul, Eldho K.
experimental part, p. 2119 - 2125 (2012/04/17)
The γ-butenolide obtained from an organocatalyzed, direct vinylogous aldol reaction of γ-crotonolactone and benzaldehyde serves as the key starting material in the expedient synthesis of a 3-hydroxy-2-phenyl piperidine intermediate which is converted to the target 2,3-disubstituted piperidines.
Organocatalytic asymmetric direct vinylogous aldol reactions of γ-crotonolactone with aromatic aldehydes
Pansare, Sunil V.,Paul, Eldho K.
supporting information; experimental part, p. 1027 - 1029 (2011/02/25)
The direct aldol reaction of γ-crotonolactone and various aromatic aldehydes is catalyzed by bifunctional aminothiourea and aminosquaramide organocatalysts to provide diastereomerically and enantiomerically enriched 5-substituted 2(5H) furanones (γ-buteno
