B. T. Cho, Y. S. Chun / Tetrahedron: Asymmetry 9 (1998) 1489–1492
1491
Table 1
a
Enantioselective addition of diethylzinc to aldehydes catalyzed by 10 mol% of 1 in toluene at 0°C
Ed. Scheffold, R. Springer-Verlag, 1989; pp. 115–198; (d) Knochel, P. In Comprehensive Organic Synthesis; Ed. Trost, B.
M. Pergamon Press, 1991; pp. 211–229.
2
. (a) Kang, J.; Kim, J. W.; Lee, J. W.; Kim, D. S.; Kim, J. I. Bull. Korean Chem. Soc. 1996, 17, 1135–1142; (b) Bolm, C.;
Schlingloff, G.; Harms, K. Chem. Ber. 1992, 125, 1191–1203; (c) Soai, K.; Hayase, T.; Takai, K.; Sugiyama, T. J. Org.
Chem. 1994, 59, 7908–7909; (d) Soai, K.; Hirose, Y.; Ohno, Y. Tetrahedron: Asymmetry, 1993, 4, 1473–1474; (e) Delair,
P.; Einhorn, C.; Einhorn, J.; Luche, J. L. Tetrahedron 1995, 51, 165–172; (f) Belliczey, J.; Giffels, G.; Kragl, U.; Wandry,
C. Tetrahedron: Asymmetry 1997, 8, 1529–1530; (g) Dosa, P. L.; Ruble, J. C.; Fu, G. C. J. Org. Chem. 1997, 62, 444–445;
(
h) Prasad, K. R. K.; Joshi, N. N. J. Org. Chem. 1997, 62, 3770–3771.
3
. (a) Cho, B. T.; Kim, N. Tetrahedron Lett. 1994, 35, 4115–4118; (b) Cho, B. T.; Kim, N.; Khoo, J.-H. Bull. Korean Chem.
Soc. 1996, 17, 1–2; (c) Cho, B. T.; Kim, N. Bull. Korean Chem. Soc. 1994, 15, 931–932; (d) Cho, B. T.; Kim, N. Synth.
Commun. 1995, 25, 167–175; (e) Cho, B. T.; Kim, N. J. Chem. Soc., Perkin Trans. 1. 1996, 2901–2907.
. Cho, B. T.; Kim, N. Synth. Commun. 1996, 26, 855–865.
4
5
6
. Cho, B. T.; Kim, N. Synth. Commun. 1996, 26, 2273–2280.
. (a) Soai, K.; Yokoyama, S.; Hayasaka, T. J. Org. Chem. 1991, 56, 4264–4268; (b) Soai, K.; Ookawa, A.; Kaba, T.; Ogawa,
K. J. Am. Chem. Soc. 1987, 109, 7111–7115.
2
0
−1
7. 1: Colorless viscous oil; [α]
D
+41.4 (c 1.13, CHCl
056, 857; H NMR (400 MHz, CDCl ) δ 0.88 (t, 6H, J=7.0 Hz), 1.26–1.48 (m, 24H), 1.34 (s, 3H), 1.36 (s, 3H), 1.40
s, 6H), 2.56–2.63 (m, 2H), 2.71–2.80 (m, 3H), 3.30 (br s, 1H), 3.48 (t, 1H, J=6.0 Hz), 3.73 (t, 1H, J=7.8 Hz), 3.84–3.89
3
); IR (neat, cm ) ν 3482, 2985, 2859, 1466, 1378, 1255, 1214, 1160,
1
1
(
(
3
1
3
m, 1H), 4.09–4.14 (m, 3H), 4.53–4.59 (m, 1H); C NMR (100 MHz, CDCl
8.14, 67.31, 65.15, 53.05, 31.86, 29.69, 29.63, 29.37, 27.42, 26.74, 26.45, 25.58, 25.10, 22.67, 14.11; anal. calcd for
: C, 69.23; H, 11.41; N, 2.88. Found: C, 69.11; H, 11.59; N,2.64.
3
) δ 109.22, 108.41, 76.23, 75.89, 70.93,
6
28 5
C H55NO