N. S. Krishnaveni et al. / Tetrahedron Letters 46 (2005) 4299–4301
4301
2. (a) Roush, W. R. In Comprehensive Organic Synthesis;
Trost, B. M., Fleming, I., Heathcock, C. H., Eds.;
Pergamon: Oxford, UK, 1991; Vol. 2; (b) Thomas, E. J.
Chem. Commun. 1997, 411.
3. (a) Nishiyama, Y.; Kakushou, F.; Sonoda, N. Tetrahedron
Lett. 2005, 46, 787, references there in; (b) Hachiya, I.;
Kobayashi, S. J. Org. Chem. 1993, 58, 6958; (c) Koba-
yashi, S.; Hachiya, I.; Yamanoi, Y. Bull. Chem. Soc. Jpn.
1994, 67, 2342.
4. (a) Yanagisawa, A.; Morodome, M.; Nakashima, H.;
Yanamoto, H. Synlett 1997, 1310; (b) Vartoli, G.; Bosco,
M.; Giuliani, A.; Marcantoni, E.; Palmieri, A.; Petrini, N.;
Sambri, L. J. Org. Chem. 2004, 69, 1290; (c) Marshall, J.
A.; Hinkel, K. W. J. Org. Chem. 1995, 60, 1290; (d) Loh,
T. P.; Xu, J. Tetrahedron Lett. 1999, 40, 2431; (e)
Kobayashi, S.; Wakabayashi, T.; Oyamada, H. Chem.
Lett. 1997, 831.
5. Lu, J.; Ji, S.-J.; Qian, R.; Chen, J.-P.; Liu, Y.; Loh, T.-P.
Synlett 2004, 534.
6. Choudary, B. M.; Jyothi, K.; Sateesh, M.; Kantam, M. L.
Synlett 2004, 231.
(b) Yadav, J. S.; Reddy, B. V. S.; Srinivas Reddy, Ch.;
Rajasekhar, K. J. Org. Chem. 2003, 68, 2525.
8. Ionic liquids cost 60–400 USD/50 g as against b-CD which
costs 105 USD/100 g.
9. (a) Breslow, R.; Dong, S. D. Chem. Rev. 1998, 98, 1997;
(b) Desper, J. M.; Breslow, R. J. Am. Chem. Soc. 1994,
116, 12081.
10. (a) Surendra, K.; Krishnaveni, N. S.; Rao, K. R. Chem.
Commun. 2005, 669; (b) Krishnaveni, N. S.; Surendra, K.;
Rao, K. R. Adv. Synth. Catal. 2004, 346, 346;
(c) Surendra, K.; Krishnaveni, N. S.; Reddy, M. A.;
Nageswar, Y. V. D.; Rao, K. R. J. Org. Chem. 2003, 68,
9119; (d) Surendra, K.; Krishnaveni, N. S.; Nageswar, Y.
V. D.; Rao, K. R. J. Org. Chem. 2003, 68, 4994; (e)
Surendra, K.; Krishnaveni, N. S.; Reddy, M. A.; Nage-
swar, Y. V. D.; Rao, K. R. J. Org. Chem. 2003, 68,
2058.
11. The reaction was carried out as follows: b-CD (1 mmol)
was dissolved in water (15 ml) by warming up to 60 °C
until a clear solution was formed and then the aldehyde
(1 mmol) dissolved in acetone (1 ml) was added slowly
with stirring. After 15 min at this temperature 2 N HCl
(1 mmol) and allyltributyltin were added and the mixture
stirred at that temperature until the reaction was complete
(Table 1). The organic material was extracted with ethyl
acetate, dried and concentrated under reduced pressure
and the resulting product, as though seen as single
compound by TLC, was further purified by passing over
a column of silica gel. The CD was recovered by filtration
and reused.
12. Schneir, H.-J.; Hacket, F.; Rudiger, V. Chem. Rev. 1998,
98, 1755.
13. Demarco, P. V.; Thakkar, A. L. Chem. Commun. 1970,
2.
14. Uekama, K.; Hirayama, F.; Irie, T. T. Chem. Rev. 1998,
98, 2045.