2
127
References
1
. (a) Wong, C. H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Tetrahedron Organic Chemistry. Pergamon:
Oxford, 1994. (b) Theil, F. Chem. Rev. 1995, 95, 2203–2227. (c) Nakamura, K.; Hirose, Y. J. Synth. Org. Chem. Jpn. 1995,
5
3, 668–677.
2
. (a) Izumi, T.; Aratani, S. J. Chem. Technol. Biotechnol. 1995, 63, 25–32. (b) Kijima, T.; Yaginuma, Y.; Izumi, T. J. Chem.
Technol. Biotechnol. 1999, 74, 501–508. (c) Ema, T.; Jittani, M.; Sakai, T.; Utaka, M. Tetrahedron Lett. 1998, 39, 6311–6314.
(d) Kazlauskas, R. J.; Weissfloch, A. N. E.; Rappaport, A. T.; Cuccia, L. A. J. Org. Chem. 1991, 56, 2656–2665. (e)
Nakamura, K.; Kawasaki, M.; Ohno, A. Bull. Chem. Soc. Jpn. 1996, 69, 1079–1085.
3
4
. (a) Fujii, I.; Togame, H.; Kanematsu, K. Chem. Pharm. Bull. 1986, 34, 4439–4442. (b) Vogtle, V. F.; Jansen, B. Tetrahedron
Lett. 1976, 52, 4895–4898.
. (a) Tsukube, H.; Betchaku, A.; Hiyama, Y.; Itoh, T. J. Chem. Soc., Chem. Commun. 1992, 1751–1752. (b) Tsukube, H.;
Betchaku, A.; Hiyama, Y.; Itoh, T. J. Org. Chem. 1994, 59, 7014–7018. (c) Muraoka, M.; Ueda, A.; Zhang, W.; Kida, T.;
Nakatsuji, Y.; Ikeda, I.; Kanehisa, N.; Kai, Y. Tetrahedron Lett. 1998, 39, 9493–9496.
5
6
. Lipase PS and AY (Amano Pharmaceutical Co.); CCL and PPL (Sigma Chemical Co.); Lipase MY and OF (Meito Sangyo
Co.); CAL (Novozyme 435 , Novo Nordisk Bio Industry Co.)
®
. Compound (±)-1 was prepared from benzo 15-crown-5 ether, by acetylation (see Ref. 11) with acetic anhydride-
polyphosphoric acid and reduction with NaBH
compound (benzo-15-crown-5 ether) and confirmed by its spectroscopic properties. H NMR (500 MHz, CDCl
4
, subsequently. (±)-1 was obtained in 77% yield of the starting crown
1
3
) δ
6
.83–6.94 (m, 3H, Cp), 4.83 (q, 1H, J=3 Hz, CH), 3.74–4.15 (m, 16H, -O-CH
2
2
-CH -), 3.44 (s, 1H, OH), 1.47 (d, 3H,
−1
J=6.5 Hz, CH
m/z: 312 M .
3
), IR ν (neat), cm : 3400 (OH), 2964 (CH
2
), 1138 (C-O-C), 941 and 860 (1,2,4-substituted benzene), MS
+
7
8
. Kazlauskas, R. J. Biotechnology; Wiley-VCH: Weinheim, 1998; Vol. 8a, pp. 37–192.
1
. H NMR (500 MHz, CDCl
s, 3H, OCH ), 1.47 (d, 3H, J=6.5 Hz, CH
. Chen, C. S.; Fujimoto, Y.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1982, 104, 7294–7299.
3
) δ 6.80–6.89 (m, 3H, Cp), 5.80 (q, 1H, J=7 Hz, CH
2 2 2
), 3.74–4.18 (m, 16H, -O-CH -CH -), 2.10
(
3
3
).
9
1
0. Trost, B. M.; Belletire, J. L.; Goldleski, S.; McDougal, P. G.; Balkovec, J. M.; Baldwin, J. J.; Christy, M. E.; Ponticello, G.
S.; Varga, S. L.; Springer, J. P. J. Am. Chem. Soc. 1986, 51, 2370–2374.
11. Wada, F.; Arata, R.; Goto, T.; Kikukawa, K.; Matsuda, T. Bull. Chem. Soc. Jpn. 1980, 53, 2061–2063.