Organocuprate-Initiated Domino Michael–Aldol Reaction
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(15 mL) and saturated aqueous NaHCO3 (15 mL), dried with
Na2SO4, filtered, and the solvents were removed under reduced
pressure to yield a yellow oil. This oil was treated with K2CO3
(105 mg, 0.758 mmol, 1 equiv.) in MeOH (8 mL) for 15 min at
room temperature to ensure complete cleavage of the TMS group
on the secondary alcohol. The reaction mixture was then diluted
with water (15 mL) and extracted with Et2O (3ϫ15 mL). Com-
bined organic layers were washed with water (15 mL) and brine
(15 mL), dried with Na2SO4, filtered, and the solvents were re-
moved under reduced pressure. Purification by flash chromatog-
raphy (neutralized silica gel; heptane/EtOAc, 3:1 to 2:1) afforded
Morita–Baylis–Hillman ester 12 (117 mg, 0.446 mmol, 59%) as a
colorless amorphous solid.
Supporting Information (see footnote on the first page of this arti-
cle): Experimental procedures, characterization data, and copies of
the NMR spectra.
[9]
Acknowledgments
This work has been financially supported by the Institut de Chimie
des Substances Naturelles (ICSN) and the Centre National pour la
Recherche Scientifique (CNRS). Dr. Xavier Guinchard is acknowl-
edged for his fruitful scientific advice and Charlotte Grosleron for
her help in the preparation of the precursors.
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Eur. J. Org. Chem. 2012, 908–912
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www.eurjoc.org
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