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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
Author(s) -
Claraz Aurélie,
Oudeyer Sylvain,
Levacher Vincent
Publication year - 2013
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201201041
Subject(s) - chemistry , aldol reaction , acetamide , furan , lewis acids and bases , amide , organic chemistry , trimethylsilyl , medicinal chemistry , catalysis
A chiral quaternary ammonium amide was generated in situ from N,O ‐bis(trimethylsilyl)acetamide (BSA) as non‐nucleophilic Brønsted 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 (5 H )‐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.