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60 °C, 30 min). Fresh portions of the starting compounds 13a, 14a,
and water were added to the remaining catalyst 11 and the reaction
was re-performed as described above. The experiments were scaled
up by using amide 11 (96 mg, 0.1 mmol), 13a (0.31 mL, 3 mmol),
14a (151 mg, 1 mmol), and distilled water (2 mL). Upon extraction
of aldol 15a with Et2O (5ϫ 5 mL), fresh portions of the starting
compounds 13a and 14a were added to the remaining suspension
of catalyst 11 in water and the reaction was re-performed.
Supporting Information (see footnote on the first page of this arti-
cle): Procedures for the preparation of each compound, 1H, 13C,
and 19F NMR spectra, HRMS spectra, and microanalysis data.
[6]
Acknowledgments
We gratefully acknowledge the financial support of the President
of the Russian Federation (Grant for Young Ph. D., number MK-
7437.2010.3) and of the Russian Foundation of Basic Research
(grant number 09-03-00384). We are also grateful to the Structural
Studies Department of the N. D. Zelinsky Institute of Organic
Chemistry (Moscow) for the NMR and high-resolution mass spec-
tra.
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