K. L. Boyle et al. / Tetrahedron Letters 47 (2006) 1311–1313
1313
7. Burk, M. J.; Kalberg, C. S.; Pizzano, A. J. Am. Chem. Soc.
1998, 120, 4345–4353.
215 nm. Retention times of 11.5 and 14.8 min repre-
sented the two enantiomers of the hydrogenated
product.
8. (a) Burk, M. J.; Harper, T. G. P.; Kalberg, C. S. J. Am.
Chem. Soc. 1995, 117, 4423–4424; (b) Mashima, K.;
Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.;
Kumobayasi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Aku-
tagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064–3076.
9. Burk, M. J.; Wang, Y. M.; Lee, J. R. J. Am. Chem. Soc.
1996, 118, 5142–5143.
10. Burk, M. J.; Harper, T. G. P.; Lee, J. R.; Kalberg, C.
Tetrahedron Lett. 1994, 35, 4963–4966.
11. Burk, M. J.; Feng, S.; Gross, M. F.; Tumas, W. J. Am.
Chem. Soc. 1995, 117, 8277–8288.
Acknowledgements
C.K. and E.B.L. would like to acknowledge the Mars
Summer Fellowship program at Wheaton College for
financial support of this project. C.K. would also like
to thank Professor Elita Pastra-Landis for helpful dis-
cussions during preparation of this manuscript.
12. (a) Xiong, W.; Lin, Q.; Ma, H.; Zheng, H.; Chen, H.; Li,
X. Tetrahedron: Asymmetry 2005, 16, 1959–1962; (b)
Yinghuai, Z.; Carpenter, K.; Bun, C. C.; Bahnmueller, S.;
Ke, C. P.; Srid, V. S.; Kee, L. W.; Hawthorne, M. F.
Angew. Chem., Int. Ed. 2003, 42, 3792–3795.
References and notes
1. Welton, T. Chem. Rev. 1999, 99, 2071–2083.
2. Earle, M.; Forestier, A.; Oiver-Bourbigou, H.; Wasser-
scheid, P. In Ionic Liquids in Synthesis; Wasserscheid, P.,
Welton, T., Eds.; Organic Synthesis; Wiley-VCH: Wein-
heim, 2003; pp 174–288.
13. (a) Berthod, M.; Joerger, J.-M.; Mignani, G.; Vaultier, M.;
Lemaire, M. Tetrahedron: Asymmetry 2004, 15, 2219–
2221; (b) Hu, A.; Ngo, H. L.; Lin, W. Angew. Chem., Int.
Ed. 2004, 43, 2501–2504; (c) Ngo, H. L.; Hu, A.; Lin, W.
Chem. Commun. 2003, 1912–1913.
3. Bonhote, P.; Dias, A.-P.; Papageorgiou, N.; Kalyanasun-
daram, K.; Gratzel, M. Inorg. Chem. 1996, 35, 1168–1178.
4. Meracz, I.; Oh, T. Tetrahedron Lett. 2003, 44, 6465–6468.
5. Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000,
39, 3772–3789.
6. (a) Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Harlow, R.
L. J. Am. Chem. Soc. 1993, 115, 10125–10138; (b)
Miyashita, A.; Takaya, H.; Souchi, T.; Noyori, R.
Tetrahedron 1984, 40, 1245–1253.
14. (a) Guernik, S.; Wolfson, A.; Herskowitz, M.; Green-
spoon, N.; Geresh, S. Chem. Commun. 2001, 2314–2315;
(b) Pugin, B.; Studer, M.; Kuesters, E.; Sedelmeier, G.;
Feng, X. Adv. Synth. Catal. 2004, 346, 1481–1486; (c)
Wolfson, A.; Vankelecom, I. F. J.; Jacobs, P. A. J.
Organomet. Chem. 2005, 690, 3558–3566.
15. (a) Schmidt, U.; Lieberknecht, A.; Wild, J. Synthesis 1984,
53–60; (b) Zoller, U.; Ben-Ishai, D. Tetrahedron 1975, 31,
863–866.