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LETTERS
SYNLETT
References
J. Org. Chem., 1993, 58, 1515. (g) Chakraborty, T. K.; Reddy, G.
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M. T.; Kesseler, K.; Jung, A. Angew. Chem. Int. Ed. Engl., 1985,
24, 989.
1.
(a) Matthews, B. R.; Gountzos, H.; Jackson, W. R.; Watson, K. G.
Tetrahedron Lett., 1989, 30, 5157. (b) Jackson, W. R.; Jacobs, H.
A.; Jayatilake, G. S.; Matthews, B. R.; Watson, K. G. Aust. J.
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Synthesis, 1990, 575. (e) Effenberger, F.; Stelzer,U. Angew.
Chem. Int. Ed. Engl., 1991, 30, 873. (f) Zandbergen, P.; Brussee,
J.; Van der Gen, A.; Kruse, C. G. Tetrahedron Asy., 1992, 3, 769.
(g) Synthesis of pharmaceutical: Watson, K. G.; Fung, Y. M.;
Gredley, M.; Bird, G. J.; Watson, W. R.; Gountzos, H.; Matthews,
B. R. J. Chem. Soc. Chem. Commun., 1990, 1018. (h) For a recent
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3.
4.
(a) Evans, D. A.; Hoffman, J. M.; Truesdale, L. K. J. Am. Chem.
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L. K. J. Org. Chem., 1974, 39, 914.
For applications of InCl in aqueous media: (a) Loh, T.-P.; Pei, J.;
3
Cao, G.-Q. J. Chem. Soc. Chem. Commun., 1996, 1819. (b) Loh,
T.-P.; Pei, J.; Lin, M. J. Chem. Soc. Chem. Commun., 1996, 2315.
(c) Li, X.-R.; Loh, T.-P.Tetrahedron Asy., 1996, 7, 1535. (d) Loh,
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(e) Loh, T.-P.; Li, X.-R. Angew. Chem. Int. Ed. Engl.,1997, 36,
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2.
(a) Corey, E. J.; Wang, Z. Tetrahedron Lett., 1993, 34, 4001.
(b) Narasaka, K.; Yamada, T.; Minamikawa, H. Chem. Lett.,
1987, 2073. (c) Minamikawa, H.; Hayakawa, S.; Yamada, T.;
Iwasawa, N.; Narasaka, K. Bull. Chem. Soc. Jpn., 1988, 61, 4379.
(d) Tsuboyama, S. Bull. Chem. Soc. Jpn., 1962, 35, 1004. (e) Kim,
H. J.; Jackson, W. R. Tetrahedron Asy., 1992, 3, 1421. (f) Nitta,
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114, 7969. (f) Hayashi, M.; Miyamoto, Y.; Inoue, T.; Oguni, N.
5.
The general procedure for InF catalysed addition of TMSCN to
3
aldehyde is as follows: To a mixture of aldehyde (0.5 mmol, 1 eq.)
and InF (0.3 eq) in water (3 mL) was added TMSCN (2 eq.). The
3
reaction mixture was stirred vigorously overnight at room
temperature. After usual extraction workup, the respective
cyanohydrins were isolated. From our experience, vigorous
stirring is very important for these organic reactions in water.