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18. Typical experimental procedure for the NH4F-catalyzed direct aldol reactions
in aqueous media (Table 2). A catalytic amount of NH4F (20 mol %) was added
to a vial containing aldehyde 2 (0.8 mmol), cyclohexanone 1a (4.0 mmol,
11. For reviews, see: (a) Davie, E. A. C.; Mennen, S. M.; Miller, Y.; Xu, S. J. Chem. Rev.
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427 lL) in H2O (150 or 260 lL). After stirring the reaction mixture for the time
shown in Table 2 at 60 °C it was loaded directly onto a silica gel column. The
crude aldol product was purified by silica gel column chromatography (EtOAc–
pentane mixtures) to furnish the desired aldol product 3.
19. Typical experimental procedure for the NH4F-catalyzed direct aldol reactions
in aqueous media (Table 3). A catalytic amount of NH4F (20 mol %) was added
to
a
vial containing 4-nitrobenzaldehyde 2a (0.8 mmol) and ketone
1
(4.0 mmol) in H2O (150
lL). After stirring the reaction mixture for the time
shown in Table 3 at 60 °C it was loaded directly onto a silica gel column. The
crude aldol product was purified by silica gel column chromatography (EtOAc–
pentane mixtures) to furnish the desired aldol product 3.
12. (a) Ooi, T.; Kameda, M.; Taniguchi, M.; Maruoka, K. J. Am. Chem. Soc. 2004, 126,
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Chem. Eur. J. 2008, 14, 40.
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20. Compound 3m: Major diastereomer. 1H NMR (400 MHz, CDCl3) d (ppm): 1.28 (t,
J = 7.2 Hz, 3H, CH3), 1.55–1.88 (m, 4H) 1.90 (m, 1H), 2.06 (m, 1H), 2.29–2.44 (m,
2H), 3.18 (dd, J = 5.5, 12.7 Hz, 1H), 4.16 (s, 1H), 4.25 (q, J = 7.1 Hz, 2H), 7.26–
7.36 (m, 3H, ArH), 7.50 (d, J = 7.2 Hz, 2H, ArH); 13C NMR (100 MHz, CDCl3) d
(ppm): 14.3, 25.6, 28.0, 30.8, 30.8, 43.2, 53.9, 62.1, 73.4, 125.8, 128.1, 128.5,
128.7, 140.6, 173.2, 212.7. Minor diastereomer. 1H NMR (400 MHz, CDCl3) d
(ppm): 1.23 (t, J = 7.2 Hz, 3H, CH3), 1,52–1.75 (m, 4H) 1.87 (m, 1H), 2.07 (m,
1H), 2.31–2.45 (m, 2H), 3.40 (dd, J = 6.1, 12.9 Hz, 1H), 3.87 (s, 1H), 4.11–4.25
(m, 2H), 7.27–7.37 (m, 3H, ArH), 7.58 (d, J = 7.9 Hz, 2H, ArH); 13C NMR
(100 MHz, CDCl3) d (ppm): 14.2, 25.1, 27.5, 27.8, 42.6, 59.0, 62.2, 77.8, 125.5,
127.9, 128.5, 139.2, 174.8, 213.0.
21. Weber, A. Orig. Life Evol. Biosph. 2007, 37, 105. In preliminary experiments, we
also found that the ammonium salt catalyzed the formation of sugars by aldol
reactions with dihydroxyacetone or glycoaldehyde in water.