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2002.
equipped with a pressure monitor. The autoclave was
completely filled with water, sealed tightly, and left in a
household electric refrigerator at )20 °C. It was found
that the internal pressure reached about 200 MPa after
12 h. After 19 h, the autoclave was taken out of the
refrigerator, and the Teflon tube was removed from the
autoclave. The reaction was quenched with phosphate
buffer and the organic materials were extracted with
ethyl acetate three times. After drying the organic phase,
volatile organic materials were removed under reduced
pressure, after which purification by thin layer chroma-
tography (hexane/ethyl acetate ¼ 1:1) afforded the aldol
product in 75% yield (31.3 mg) with 4-(p-nitrophenyl)-3-
butene-2-one (3%) and recovered p-nitrobenzaldehyde
(20%). The enantiomeric excess of the aldol is 75%,
which was determined by chiral HPLC analysis.
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Acknowledgements
This work was supported by a Grant-in-Aid for Scien-
tific Research on Priority Areas (A) ‘Exploitation of
Multi-Element Cyclic Molecules’ from the Ministry of
Education, Culture, Sports, Science and Technology,
Japan. Y. H. thanks Dr. Kiyoshi Hayakawa at the
Kyoto Prefectural Comprehensive Center for small and
medium enterprises for instruction concerning the
pressure induced by water freezing.
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