Toshiyuki Oyama,* Hiroki Yoshioka and Masao Tomoi
Department of Advanced Materials Chemistry, Faculty of Engineering,
Yokohama National University, 79-5 Tokiwadai, Hodogaya-ku,
Yokohama, 240-8501, Japan. E-mail: oyama1@ynu.ac.jp;
Fax: +81 45 339 3961; Tel: +81 45 339 3961
M. Shiro and S. Hashimoto, J. Am. Chem. Soc., 1998, 120, 6419; (c)
K. Iseki, S. Mizuno, Y. Kuroki and Y. Kobayashi, Tetrahedron, 1999,
55, 977; (d) S. Kobayashi, C. Ogawa, H. Konishi and M. Sugiura,
J. Am. Chem. Soc., 2003, 125, 6610.
5 Examples of the polymers containing achiral phosphoramide structures:
(a) M. Tomoi, M. Ikeda and H. Kakiuchi, Tetrahedron Lett., 1978, 39,
3757; (b) T. Oyama, Y. Ohkubo, K. Naka and Y. Chujo, Polym. J.,
1998, 30, 1008; (c) T. Oyama, Y. Ohkubo, K. Naka and Y. Chujo,
Polym. J., 1999, 31, 506; (d) R. A. Flowers, II, X. Xu, C. Timmons and
G. Li, Eur. J. Org. Chem., 2004, 2988.
6 For recent reviews on polymer-supported catalysts, see: (a) T. Frenzel,
W. Solodenko and A. Kirschning, in Polymeric Materials in Organic
Synthesis and Catalysis, ed. M. R. Buchmeiser, Wiley-VCH, Weinheim,
2003, ch. 4; (b) T. J. Dickerson, N. N. Reed and K. D. Janda, in
Polymeric Materials in Organic Synthesis and Catalysis, ed. M. R.
Buchmeiser, Wiley-VCH, Weinheim, 2003, ch. 5; (c) Chiral Catalyst
Immobilization and Recycling, ed. D. E. De Vos, I. F. J. Vankelecom
and P. A. Jacobs, Wiley-VCH, Weinheim, 2000.
Notes and references
1 For recent reviews, see: (a) B. List, Tetrahedron, 2002, 58, 5573; (b)
R. O. Duthaler, Angew. Chem. Int. Ed., 2003, 42, 975; (c) K. Maruoka
and T. Ooi, Chem. Rev., 2003, 103, 3013; (d) S. France, D. J. Guerin,
S. J. Miller and T. Lectka, Chem. Rev., 2003, 103, 2985; (e) Acc. Chem.
Res., 2004, 37(8) (special issue on asymmetric organocatalysis).
2 Reviews on the Lewis base-catalysed asymmetric allylations: (a)
S. E. Denmark and J. Fu, Chem. Rev., 2003, 103, 2763; (b)
S. E. Denmark and J. Fu, Chem. Commun., 2003, 167. For a review
on the asymmetric aldol reaction, see: (c) S. E. Denmark and
R. A. Stavenger, Acc. Chem. Res., 2000, 33, 432.
7 Examples of allylation and aldol reactions catalysed by polymer-
supported achiral Lewis bases: (a) C. Ogawa, M. Sugiura and
S. Kobayashi, Chem. Commun., 2003, 192; (b) reference 5d.
3 (a) S. E. Denmark, D. M. Coe, N. E. Pratt and B. D. Griedel, J. Org.
Chem., 1994, 59, 6161; (b) K. Iseki, Y. Kuroki, M. Takahashi,
S. Kishimoto and Y. Kobayashi, Tetrahedron, 1997, 53, 3513; (c)
S. E. Denmark and J. Fu, J. Am. Chem. Soc., 2000, 122, 12021; (d)
S. E. Denmark and J. Fu, J. Am. Chem. Soc., 2001, 123, 9488; (e)
S. E. Denmark and J. Fu, J. Am. Chem. Soc., 2003, 125, 2208.
4 (a) R. M. Angell, A. G. M. Barrett, D. C. Braddock, S. Swallow and
B. D. Vickery, Chem. Commun., 1997, 919; (b) M. Nakajima, M. Saito,
8 A. Alexandre, S. Mutti and P. Mangeney, J. Org. Chem., 1992, 57, 1224.
9
1H–NMR spectra of the homopolymers and the representative
copolymers are shown in ESI.
10 S. E. Denmark, X. Su, Y. Nishigaichi, D. M. Coe, K.-T. Wong, S. B.
D. Winter and J. Y. Choi, J. Org. Chem., 1999, 64, 1958.
This journal is ß The Royal Society of Chemistry 2005
Chem. Commun., 2005, 1857–1859 | 1859