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University. One of the authors (K.K.) is grateful for a Sasakawa
Scientific Research Grant from the Japan Science Society.
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Supplementary data
Supplementary data (experimental procedures and spectral
data.) associated with this article can be found, in the online ver-
13. Guillena, G.; Nájera, C.; Viózquez, S. F. Synlett 2008, 3031, and references cited
therein.
14. Perlmutter, P. Conjugate Additions in Organic Synthesis; Pergamon: Oxford, 1992.
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17. Compound 3f: pKa 6.94; 3h, pKa 6.37. See Ref. 3. See also: (a) Brotzel, F.; Kempf,
B.; Singer, T.; Zipse, H.; Mayr, H. Chem.-Eur. J. 2007, 13, 336; (b) Wei, Y.; Sastry,
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19. Light microscopic studies could not confirm the fact that the reaction occurred
in the micelles in water.
20. For the Michael addition reactions in EtOH in the absence of any catalysts, see:
Shirakawa, S.; Shimizu, S. Synlett 2007, 3160.
21. As background experiments, in the absence of catalyst 3d no reaction was
observed in water or in MeOH.
22. Typical experimental procedure for Michael addition reaction in water. Preparation
References and notes
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of 4b: To
a stirred solution of methyl cyclopentan-1-one-2-carboxylate
(142 mg, 1.0 mmol) and 4-didecylaminopyridine (37.4 mg, 0.1 mmol) in H2
O
(2.0 mL) was added methyl acrylate (172 mg, 2.0 mmol), and the mixture was
stirred at rt for 1.5 h. After the reaction was quenched by the addition of satd
NaHCO3, the mixture was thoroughly extracted with AcOEt. The crude product
was purified by silica gel column chromatography (elution with hexane/
AcOEt = 2:1) to give 227 mg (99%) of 4b as a colorless oil.