Communications
Keywords: asymmetric catalysis · Brønsted acids · Morita–
.
Baylis–Hillman reaction · organocatalysis · phosphanes ·
synthetic methods
[1] a) A. T. Merritt, S. V. Ley, Nat. Prod. Rep. 1992, 9, 243; b) T. J.
Tokoroyama, Synth. Org. Chem. Jpn. 1993, 51; c) J. R. Hanson,
Nat. Prod. Rep. 2002, 19, 125.
[2] a) B. R. Copp, Nat. Prod. Rep. 2003, 20, 535; b) J. R. Hanson,
Nat. Prod. Rep. 2005, 22, 594.
[3] a) Y. Tesfamariam, A. Rudi, S. Zafra, I. Goldberg, G. Gravalos,
M. Chleyer, Y. Kashman Tetrahedron Lett. 1998, 39, 3323; b) T.
Yosief, A. Rudi, Y. Kashman, J. Nat. Prod. 2000, 63, 299.
[4] J. R. Carney, P. J. Scheuer, Tetrahedron Lett. 1993, 34, 3727.
[5] D. Pappo, S. Shimony, Y. Kashman, J. Org. Chem. 2005, 70, 199.
[6] a) H. Kawano, M. Itoh, T. Katoh, S. Terashima, Tetrahedron Lett.
1997, 38, 7769; b) A. X. Xiang, D. A. Watson, T. Ling, E. A.
Theodorakis, J. Org. Chem. 1998, 63, 6774; c) I. E. Marko, M.
Wiaux, S. M. Warriner, P. R. Giles, P. Eustace, D. Dean, M.
Bailey, Tetrahedron Lett. 1999, 40, 5629; d) A. S. Kende, J. J.
Rustenhoven, K. Zimmermann, Tetrahedron Lett. 2000, 41, 843;
e) T. T. Ling, F. Rivas, E. A. Theodorakls, Tetrahedron Lett.
2002, 43, 9019.
[7] a) T. Tokoroyama, M. Asada, H. Iio, Tetrahedron Lett. 1984, 25,
5070; b) M. Tsukamoto, T. Asada, H. Iio, T. Tokoroyama,
Tetrahedron Lett. 1987, 28, 6645; c) T. Tokoroyama, H. Iio, K.
Okada, J. Chem. Soc. Chem. Commun. 1989, 1572; d) T. Aoto, T.
Tokoroyama, J. Org. Chem. 1998, 63, 4151; e) P. Wasnaire, M.
Wiaux M, R. Touillaux, I. E. Markꢀ, Tetrahedron Lett. 2006, 47,
985.
[8] a) N. T. McDougal, S. E. Schaus, J. Am. Chem. Soc. 2003, 125,
12024; b) N. T. McDougal, W. L. Trevellini, S. A. Rodgen, L. T.
Kliman, S. E. Schaus, Adv. Synth. Catal. 2004, 346, 1231.
[9] M. Tsukamoto, H. Iio, T. Tokoroyama, Tetrahedron Lett. 1984,
25, 5067.
[10] For reviews on the synthetic utility of the MBH reaction, see:
a) D. Basavaiah, A. J. Rao, T. Satyanarayana, Chem. Rev. 2003,
103, 811; b) E. Ciganek, Org. React. 1997, 51, 201; c) D.
Basavaiah, P. D. Rao, R. S. Hyma, Tetrahedron 1996, 52, 8001;
d) S. E. Drewes, G. H. P. Roos, Tetrahedron 1988, 44, 4653.
[11] Reviews: a) E. Langkopf, D. Schinzer, Chem. Rev. 1995, 95, 1375;
b) M. A. Varner, R. B. Grossman, Tetrahedron 1999, 55, 13867;
examples: c) J. M. Luteijn, A. de Groot, J. Org. Chem. 1981, 46,
3448; d) G. Majetich, R. Desmond, A. M. Casares, Tetrahedron
Lett. 1983, 24, 1913; e) P. S. Jones, S. V. Ley, N. S. Simpkins, A. J.
Whittle, Tetrahedron 1986, 42, 6519; f) G. Majetich, R. W.
Desmond, Jr., J. J. Soria, J. Org. Chem. 1986, 51, 1753; g) T.
Tokoroyama, K. Okada, H. Iio, J. Chem. Soc. Chem. Commun.
1989, 1572; h) H. Boushard, J. Y. Lallemand, Tetrahedron Lett.
1990, 31, 5151; i) C. Dufresne, D. Cretney, C. K. Lau, V. Mascitti,
N. Tsou, Tetrahedron: Asymmetry 2002, 13, 1965.
[12] a) A. Hosomi, H. Sakurai, Tetrahedron Lett. 1976, 1295; b) E. W.
Colvin, Chem. Soc. Rev. 1978, 7, 15.
[13] a) S. R. Wilson, M. F. Price, J. Am. Chem. Soc. 1982, 104, 1124;
b) K. Nonoshita, H. Banno, K. Maruoka, H. Yamamoto, J. Am.
Chem. Soc. 1990, 112, 316; c) R. T. Beresis, J. S. Solomon, M. G.
Yang, N. F. Jain, J. S. Panek, Org. Synth. 1997, 75, 78.
[14] J. D. More, N. S. Finney, Org. Lett. 2002, 4, 3001.
[15] a) E. J. Corey, R. K. Bakshi, S. Shibata, J. Am. Chem. Soc. 1987,
109, 5551; b) E. J. Corey, C. J. Helal, Angew. Chem. 1998, 110,
2092; Angew. Chem. Int. Ed. 1998, 37, 1986.
[16] J. C. Anderson, D. J. Pearson, J. Chem. Soc. Perkin Trans. 1 1998,
2023.
[17] For Brønsted acid catalyzed [3,3] sigmatropic rearrangements,
see: a) L. H. Kuo, D. P. Curran, Tetrahedron Lett. 1995, 36, 6647;
b) G. Nordmann, S. L. Buchwald, J. Am. Chem. Soc. 2003, 125,
4978.
ꢀ 2006 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Angew. Chem. Int. Ed. 2006, 45, 4929 –4932