Yu. N. Belokon, A. J. Blacker, L. A. Clutterbuck, D. Hogg, M. North, C. Reeve
FULL PAPER
[14]
[15]
For a review of the development and applications of catalyst 1
see: T. R. J. Achard, L. A. Clutterbuck, M. North, Synlett
2005, 1828–1847.
the EPSRC national mass spectrometry service at the University of
Wales, Swansea, and use of the EPSRC’s Chemical Database Ser-
vice at Daresbury is also gratefully acknowledged.
For the use of other (salen)metal complexes in asymmetric cya-
nohydrin synthesis see: a) I. P. Holmes, H. B. Kagan, Tetrahe-
dron Lett. 2000, 41, 7457–7460; b) D. A. Nicewicz, C. M. Yates,
J. S. Johnson, Angew. Chem. Int. Ed. 2004, 43, 2652–2655; c)
D. A. Nicewicz, C. M. Yates, J. S. Johnson, J. Org. Chem. 2004,
69, 6548–6555; d) F.-X. Chen, H. Zhou, X. Liu, B. Qin, X.
Feng, G. Zhang, Y. Jiang, Chem. Eur. J. 2004, 10, 4790–4797;
e) S. S. Kim, D. H. Song, Eur. J. Org. Chem. 2005, 1777–1780;
f) S. S. Kim, S. H. Lee, Synth. Commun. 2005, 35, 751–759; g)
S. S. Kim, J. M. Kwak, Tetrahedron 2006, 62, 49–53.
a) Y. N. Belokon, S. Caveda-Cepas, B. Green, N. S. Ikonnikov,
V. N. Khrustalev, V. S. Larichev, M. A. Mosckalenko, M.
North, C. Orizu, V. I. Taravov, M. Tasinazzo, G. I. Timofeeva,
L. V. Yashkina, J. Am. Chem. Soc. 1999, 121, 3968–3973; b)
Y. N. Belokon, B. Green, N. S. Ikonnikov, M. North, V. I. Tara-
rov, Tetrahedron Lett. 1999, 40, 8147–8150.
a) Y. N. Belokon, J. Blacker, L. A. Clutterbuck, M. North, Org.
Lett. 2003, 23, 4505–4507; b) Y. N. Belokon, E. Ishibashi, H.
Nomura, M. North, Chem. Commun. 2006, 1775–1777.
S. Lundgren, E. Wingstrand, M. Penhoat, C. Moberg, J. Am.
Chem. Soc. 2005, 127, 11592–11593.
a) Y. N. Belokon, A. V. Gutnov, M. A. Moskalenko, L. V.
Yashkina, D. E. Lesovoy, N. S. Ikonnikov, V. S. Larichev, M.
North, Chem. Commun. 2002, 244–245; b) Y. N. Belokon, P.
Carta, A. V. Gutnov, V. Maleev, M. A. Moskalenko, L. V.
Yashkina, N. S. Ikonnikov, N. V. Voskoboev, V. N. Khrustalev,
M. North, Helv. Chim. Acta 2002, 85, 3301–3312.
a) C. Baleizão, B. Gigante, H. Garcia, A. Corma, J. Catal.
2003, 215, 199–207; b) C. Baleizão, B. Gigante, D. Das, M.
Alvaro, H. Garcia, A. Corma, Chem. Commun. 2003, 1860–
1861; c) C. Baleizão, B. Gigante, H. Garcia, A. Corma, Tetra-
hedron 2004, 60, 10461–10468; d) C. Baleizão, B. Gigante, H.
Garcia, A. Corma, J. Catal. 2004, 221, 77–84.
[1] For a review of this area see: S. J. Broadwater, S. L. Roth, K. E.
Price, M. Kobasˇlija, D. T. McQuade, Org. Biomol. Chem. 2005,
3, 2899–2906.
[2] a) B. R. Matthews, H. Gountzos, W. R. Jackson, K. G. Watson,
Tetrahedron Lett. 1989, 30, 5157–5158; b) T. Ziegler, B. Horsch,
F. Effenberger, Synthesis 1990, 575–578.
[3] a) W. R. Jackson, H. A. Jacobs, G. S. Jayatilake, B. R. Mat-
thews, K. G. Watson, Aust. J. Chem. 1990, 43, 2045–2062; b)
W. R. Jackson, H. A. Jacobs, B. R. Matthews, G. S. Jayatilake,
K. G. Watson, Tetrahedron Lett. 1990, 31, 1447–1450.
[4] a) F. Effenberger, U. Stelzer, Angew. Chem. Int. Ed. Engl. 1991,
30, 873–874; b) P. Zandbergen, J. Brussee, A. van der Gen,
C. G. Kruse, Tetrahedron: Asymmetry 1992, 3, 769–774.
[5] For reviews of the synthesis and applications of chiral cyanohy-
drins see: a) M. North, Tetrahedron: Asymmetry 2003, 14, 147–
176; b) J.-M. Brunel, I. P. Holmes, Angew. Chem. Int. Ed. 2004,
43, 2752–2778.
[6] a) A. Mori, H. Nitta, M. Kudo, S. Inoue, Tetrahedron Lett.
1991, 32, 4333–4336; b) H. Abe, H. Nitta, A. Mori, S. Inoue,
Chem. Lett. 1992, 2443–2446; c) H. Nitta, D. Yu, M. Kudo, A.
Mori, S. Inoue, J. Am. Chem. Soc. 1992, 114, 7969–7975.
[7] For recent examples see: a) J. Casas, C. Nájera, J. M. Sansano,
J. M. Saá, Tetrahedron 2004, 60, 10487–10496; b) B. He, F.-X.
Chen, Y. Li, X. Feng, G. Zhang, Eur. J. Org. Chem. 2004, 4657–
4666; c) Y. Li, B. He, B. Qin, X. Feng, G. Zhang, J. Org. Chem.
2004, 69, 7910–7913; d) B. M. Trost, S. Martínez-Sánchez, Syn-
lett 2005, 627–630; e) Y.-C. Qin, L. Liu, L. Pu, Org. Lett. 2005,
7, 2381–2383; f) M. Hatano, T. Ikeno, T. Miyamoto, K. Ishih-
ara, J. Am. Chem. Soc. 2005, 127, 10776–10777; g) X. Liu, B.
Qin, X. Zhou, B. He, X. Feng, J. Am. Chem. Soc. 2005, 127,
12224–12225; h) M. Suzuki, N. Kato, M. Kanai, M. Shibasaki,
Org. Lett. 2005, 7, 2527–2530.
[16]
[17]
[18]
[19]
[20]
[21]
[22]
[23]
[24]
[25]
M. North, A. W. Parkins, A. N. Shariff, Tetrahedron Lett. 2004,
45, 7625–7627.
Y. N. Belokon, P. Carta, M. North, Tetrahedron Lett. 2005, 46,
4483–4486.
Y. Lu, C. Miet, N. Kunesch, J. E. Poisson, Tetrahedron: Asym-
metry 1993, 4, 893–902.
[8] W. Huang, Y. Song, J. Wang, G. Cao, Z. Zheng, Tetrahedron
2004, 60, 10469–10477.
[9] a) J. Casas, A. Baeza, J. M. Sansano, C. Nájera, J. M. Saá,
Tetrahedron: Asymmetry 2003, 14, 197–200; b) N. Yamagiwa,
J. Tian, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2005,
127, 3413–3422.
[10] A. Baeza, C. Nájera, J. M. Sansano, J. M. Saá, Chem. Eur. J.
2005, 11, 3849–3862.
T. Sakai, Y. Miki, M. Nakatani, T. Ema, K. Uneyama, M.
Utaka, Tetrahedron Lett. 1998, 39, 5233–5236.
a) N. W. Fadnavis, R. L. Babu, G. Sheelu, A. Deshpande, Tet-
rahedron: Asymmetry 2001, 12, 1695–1699; b) N. W. Fadnavis,
R. R. Kasiraman, K. V. Madhuri, Tetrahedron: Asymmetry
2004, 15, 549–553.
a) M. Inagaki, J. Hiratake, T. Nishioka, J. Oda, J. Org. Chem.
1992, 57, 5643–5649; b) N. W. Fadnavis, R. L. Babu, G. Sheelu,
A. Deshpande, Tetrahedron: Asymmetry 2000, 11, 3303–3309;
c) C. Paizs, P. Tähtinen, K. Lundell, L. Poppe, F.-D. Irimie,
L. T. Kanerva, Tetrahedron: Asymmetry 2003, 14, 1895–1904;
d) G. de Gonzalo, I. Lavandera, R. Brieva, V. Gotor, Tetrahe-
dron 2004, 60, 10525–10532.
R. Zhou, J. H. Xu, Biochem. Eng. J. 2005, 23, 11–15.
U. Hanefeld, Y. Li, R. A. Sheldon, T. Maschmeyer, Synlett
2000, 12, 1775–1776.
T. Zhang, L. Yang, Z. Zhu, J. Wu, J. Mol. Catal. B 2002, 18,
315–323.
N. Nakajima, M. Saito, M. Ubukata, Tetrahedron 2002, 58,
3561–3577.
L. Veum, M. Kuster, S. Telalovic, U. Hanefeld, T. Maschmeyer,
Eur. J. Org. Chem. 2002, 1516–1522.
M. Schmidt, S. Herve, N. Klempier, H. Griengl, Tetrahedron
1996, 52, 7833–7840.
J. M. Photis, J. Org. Chem. 1981, 46, 182–184.
E. Baciocchi, M. Mattioli, R. Romano, R. Ruzziconi, J. Org.
Chem. 1991, 56, 7154–7160.
[11] For reviews see: a) R. J. H. Gregory, Chem. Rev. 1999, 99,
3649–3682; b) F. Effenberger, S. Forster, H. Wajant, Curr. Opin.
Biotechnol. 2000, 11, 532–539; c) H. Griengl, H. Schwab, M.
Fechter, Trends Biotechnol. 2000, 18, 252–256; d) J. Sukuma-
ran, U. Hanefeld, Chem. Soc. Rev. 2005, 34, 530–542.
[12] a) M. Inagaki, J. Hiratake, T. Nishioka, J. Oda, J. Am. Chem.
Soc. 1991, 113, 9360–9361; b) M. Inagaki, J. Hiratake, T. Ni-
shioka, J. Oda, J. Org. Chem. 1992, 57, 5643–5649; c) E.
Vänttinen, L. T. Kanerva, Tetrahedron: Asymmetry 1995, 6,
1779–1786; d) U. Hanefeld, A. J. J. Straathof, J. J. Heijnen, J.
Mol. Catal. B 2001, 11, 213–218; e) Y.-X. Li, A. J. J. Straathof,
U. Hanefeld, Tetrahedron: Asymmetry 2002, 13, 739–743; f) C.
[26]
[27]
[28]
Paizs, M. Tosa, C. Majdik, P. Tähtinen, F. D. Irimie, L. T.
¸
Kanerva, Tetrahedron: Asymmetry 2003, 14, 619–627; g) L.
Veum, U. Hanefeld, Tetrahedron: Asymmetry 2004, 15, 3707–
3709; h) L. Veum, L. T. Kanerva, P. J. Halling, T. Maschmeyer,
U. Hanefeld, Adv. Synth. Catal. 2005, 347, 1015–1021; i) L.
Veum, U. Hanefeld, Synlett 2005, 2382–2384.
[29]
[30]
[31]
[32]
[13] a) H. Gröger, Adv. Synth. Catal. 2001, 343, 547–558; b) Y.-
X. Li, A. J. J. Straathof, U. Hanefeld, Tetrahedron: Asymmetry
2002, 13, 739–743; c) M. Kimura, A. Kuboki, T. Sugai, Tetra-
hedron: Asymmetry 2002, 13, 1059–1068; d) C. Paizs, M. Tosa,
C. Majdik, P. Tähtinen, F. D. Irimie, L. T. Kanerva, Tetrahe-
dron: Asymmetry 2003, 14, 619–627; e) C. Paizs, P. Tähtinen,
M. Tosa, C. Majdik, F.-D. Irimie, L. T. Kanerva, Tetrahedron
2004, 60, 10533–10540.
[33]
[34]
4616
www.eurjoc.org
© 2006 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Eur. J. Org. Chem. 2006, 4609–4617