A. Kamal, G. B. Ramesh Khanna / Tetrahedron: Asymmetry 12 (2001) 405–410
409
2H), 5.20–5.33 (m, 1H), 4.14 (dd, J1=3.57 Hz, J2=9.52
References
Hz, 1H), 4.05 (dd, J1=4.76 Hz, J2=10.71 Hz, 1H), 2.88
(d, J=4.76 Hz, 2H), 2.28 (s, 3H), 2.13 (s, 3H); MS: m/z
233, 126, 108, 91.
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4.3.11.
3-Acetyloxy-4-(4-chlorophenoxy)-(3R)-butane-
nitrile (R)-3d. Resolution of 4-(4-chlorophenoxy)-3-
hydroxybutanenitrile 2d by employing the above gen-
eral procedure for the resolution of b-hydroxy nitriles
afforded (R)-3d in 45% yield and 92.1% e.e. [h]2D5=+
26.7 (c 1.0, CHCl3); IR (film): 3071, 2938, 2255, 1742,
1373, 1212, 1047 cm−1; H NMR (200 MHz, CDCl3): l
1
7.21 (d, J=7.69 Hz, 2H), 6.80 (d, J=7.69 Hz, 2H),
5.20–5.31 (m, 1H), 4.00–4.20 (m, 2H), 2.73–2.97 (m,
2H), 2.11 (s, 3H); MS: m/z 253, 148, 125.
4.3.12.
3-Acetyloxy-4-(4-bromophenoxy)-(3R)-butane-
nitrile (R)-3e. Resolution of 4-(4-bromophenoxy)-3-
hydroxybutanenitrile 2e by employing the above gen-
eral procedure for the resolution of b-hydroxy nitriles
afforded (R)-3e in 55% yield and 88.7% e.e. [h]2D5=+
29.45 (c 0.5, CHCl3); IR (film): 3023, 2937, 2255, 1755,
1373, 1246, 1045 cm−1; H NMR (200 MHz, CDCl3): l
1
7.38 (d, J=6.02 Hz, 2H), 6.76 (d, J=6.02 Hz, 2H),
5.20–5.30 (m, 1H), 4.00–4.19 (m, 2H), 2.74–2.95 (m,
2H), 2.11 (s, 3H); MS: m/z 297, 299, 187, 185, 174, 172.
7. (a) Kamal, A.; Damayanthi, Y.; Reddy, B. S. N.; Laxmi-
narayana, B.; Reddy, B. S. P. Chem. Commun. 1997,
1015; (b) Kamal, A.; Damayanthi, Y.; Rao, M. V. Tetra-
hedron: Asymmetry 1992, 3, 1361; (c) Kamal, A.; Rao, M.
V. Tetrahedron: Asymmetry 1994, 5, 1881.
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T.; Hiyama, Y.; Tsukube, H. J. Org. Chem. 1996, 61,
2158.
4.3.13. 3-Acetyloxy-4-(1-naphthyloxy)-(3R)-butanenitrile
(R)-3f. Resolution of 3-hydroxy-4-(1-naphthyloxy)-
butanenitrile 2f by employing the general procedure at
40°C afforded (R)-3f in 36% yield and >98.0% e.e.
[h]2D5=+26.8 (c 1.0, CHCl3); IR (film): 3059, 2937, 2255,
1742, 1393, 1218, 1105 cm−1; 1H NMR (200 MHz,
CDCl3): l 8.13–8.20 (m, 1H), 7.75–7.83 (m, 1H), 7.25–
7.52 (m, 4H), 6.8 (d, J=7.14 Hz, 1H), 5.41–5.52 (m,
1H), 4.26–4.40 (m, 2H), 2.97 (d, J=4.76 Hz, 2H), 2.18
(s, 3H); MS: m/z 269, 164, 126.
9. (a) Itoh, T.; Takagi, Y.; Fujisawa, T. Tetrahedron Lett.
1989, 30, 3811; (b) Fuganti, C.; Pedrocchi-Fantoni, G.;
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39, 5121.
4.3.14. 3-Acetyloxy-4-(2-naphthyloxy)-(3R)-butanenitrile
(R)-3g. Resolution of 3-hydroxy-4-(2-naphthyloxy)-
butanenitrile 2g by employing the general procedure for
the resolution of b-hydroxy nitriles at 40°C afforded
(R)-3g in 34% yield and >99.0% e.e. Mp 77–80°C;
[h]2D5=+34.13 (c 0.8, CHCl3); IR (KBr): 3073, 2926,
2250, 1739, 1374, 1249, 1037 cm−1; 1H NMR (200
MHz, CDCl3): l 7.68–7.75 (m, 3H), 7.24–7.46 (m, 2H),
7.08–7.13 (m, 2H), 5.28–4.00 (m, 1H), 4.16–4.31 (m,
2H), 2.91 (d, J=3.61 Hz, 2H), 2.16 (s, 3H); MS: m/z
267, 144, 115.
10. Florey, P.; Smallridge, A. J.; Ten, A.; Trewhella, M. A.
Org. Lett. 1999, 1, 1879.
11. (a) Victor. L. (Orsymonde, S. A.) Ger. Offen. 2,132,113
1972, Jan 05; (b) Orsymonde, S. A. Ger. Offen. 2,239,606
1973, Feb 15; (c) Orsymonde, S. A. Fr. Demande
2,205,316 1974, May 31; (d) Kalman, H.; Dezso, K.;
Erzsebet, M.; Jozsef, S. Ger. Offen. 2,506,355 1975, Aug
21; (e) Victor, L. (Orsymonde, S. A.) Ger. Offen.
2,166,869 1976, May 06.
12. (a) Smith, J. G. Synthesis 1984, 629; (b) Nagata, W.;
Yoshioka, M.; Okumura, T. J. Chem. Soc. C 1970, 17,
2365.
Acknowledgements
13. Chini, M.; Crotti, P.; Favero, L.; Macchia, F. Tetra-
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1990, 31, 6209.
The authors are grateful to Amano Pharmaceutical Co.
and Novo Nordisk for providing the gift samples of
Amano PS lipase and Lipozyme, respectively. One of
the authors (G.B.R.K.) thanks CSIR, New Delhi for
the award of a research fellowship.
15. Mitchell, D.; Koenig, T. M. Tetrahedron Lett. 1992, 33,