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LETTER
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(6) For pioneering examples, see: (a) Hayashi, T.; Tanaka, K.;
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Y.-J.; Jenkins, P.; McMorn, P.; Landon, P.; Enache, D. I.;
Carley, A. F.; Attard, G. A.; Hutchings, G. J.; King, F.; Stitt,
E. H.; Johnston, P.; Griffin, K.; Kiely, C. J. Nature (London)
2005, 437, 1132.
(7) Sawaki, Y.; Ogata, Y. J. Am. Chem. Soc. 1975, 97, 6983.
(8) (a) Russel, G. A.; Jansen, E. G.; Bemis, A. G.; Geels, E. J.;
Moye, A. J.; Mak, S.; Strom, E. T. Adv. Chem. Ser. 1965, 51,
112. (b) Russel, G. A.; Bemis, A. G.; Geels, E. J.; Jansen, E.
G.; Moye, A. Adv. Chem. Ser. 1968, 75, 174.
(9) General Procedure for Auto-Oxidation-Type Reaction of
Compound 1 Catalyzed by Au:PVP under DBU/H2O–
MeCN Conditions
(11) (a) Masui, M.; Ando, A.; Shioiri, T. Tetrahedron Lett. 1988,
29, 2835. (b) De Vries, E. F. J.; Ploeg, L.; Colao, M.;
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Tetrahedron Lett. 2000, 41, 1385. (f) Christoffers, J.;
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(12) General Procedure for a-Hydroxylation of Compound 1
Catalyzed by Au:PVP under NaOAc/DMSO Conditions
A test tube (f = 30 mm) was placed with 1 (0.1 mmol),
NaOAc (8.2 mg, 0.10 mmol), and dried Au:PVP (22.9 mg,
3 atom%). DMSO (6 mL) was added, and the reaction
mixture was stirred vigorously (1300 rpm) at 27 °C or 50 °C
for the time specified. The reaction mixture was extracted
with EtOAc and then the combined organic layers were
washed with brine, dried over Na2SO4, and concentrated in
vacuo. Purification of the product was carried out by PTLC
or GPC.
A test tube (f = 30 mm) was placed with 1 (0.10 mmol),
DBU (30 mL, 0.20 mmol), and MeCN (3 mL). The aq soln of
Au:PVP (0.5 mM, 6 mL = 3 atom%) was added and the
reaction mixture was stirred vigorously (1300 rpm) at 27 °C
or 50 °C for the time specified. The reaction mixture was
quenched with 1 M HCl (2 mL) solution, extracted with
MTBE (3 × 10 mL), and then the combined organic layers
were washed with brine, dried over Na2SO4, and
concentrated in vacuo. The crude products were separated by
PTLC (Wakogel BF-5) or GPC, giving 2 and 3.
Compound 3b: colorless oil. IR (neat): n = 3445, 1710, 1608,
1509, 1254 cm–1. 1H NMR (400 MHz, CDCl3): d = 2.25 (s,
3 H), 3.81 (s, 3 H), 4.79 (s, 1 H), 6.88–6.90 (m, 2 H), 7.25–
7.28 (m, 2 H), 7.35–7.38 (m, 5 H) ppm. 13C NMR (100 MHz,
CDCl3): d = 208.76, 159.40, 141.41, 133.32, 129.35, 128.43,
128.16, 128.03, 113.80, 85.33, 55.29, 26.07 ppm. Anal.
Calcd for C16H16O3: C, 74.98; H, 6.29; Found: C, 74.71; H,
6.37.
(10) Chen, B.-C.; Zhou, P.; Davis, F. A.; Ciganek, E. Org. React.
2003, 62, 1.
Synlett 2009, No. 2, 245–248 © Thieme Stuttgart · New York