Enantioselective Addition of Diethylzinc to Aldehydes Catalyzed by Chiral Hydroxymethylthiazolidines

Sang-Han Kim; Sung-Taik Chung; Myung-Jong Jin

Journal of Industrial and Engineering Chemistry, Vol.4, No.4, 345-347, December, 1998

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Enantioselective Addition of Diethylzinc to Aldehydes Catalyzed by Chiral Hydroxymethylthiazolidines

Sang-Han Kim, Sung-Taik Chung, and Myung-Jong Jin^†

Department of Chemical Engineeing, Inha University, Inchon 402-751, Korea

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A series of chiral thiazolidine-based β-amino alcohols 2a-c was readily synthesized from enantiomerically pure L-cysteine ethyl ester hydrochloride. These compounds could be used as chiral catalysts in enantioselective addition of diethylzinc to aldehydes. Particularly, 2c was found to be the most efficient catalyst, which produced optically active secondary alcohols with moderate enantioselectivity (up to 76% ee) in good yield.

Keywords:Asymmetric Catalysis;Diethylzinc-aldehyde Addition;Hydroxymethylthiazo- lidine

[References]

For reviews on Asymmetric Catalysis see: R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley-Interscience, New York (1993)
Noyori R, Kitamura M, Angew. Chem.-Int. Edit., 30, 49 (1991)
Soai K, Niwa S, Chem. Rev., references cited herein, 92, 833 (1992)
Oguni N, Omi T, Tetrahedron Lett., 25, 2823 (1984)
Kitamura M, Suga S, Kawai K, Noyori R, J. Am. Chem. Soc., 108, 6071 (1986)
Kitamura M, Okada S, Suga S, Noyori R, J. Am. Chem. Soc., 111, 4028 (1989)
Soai K, Yokoyama S, Hayasaka T, J. Org. Chem., 56, 4264 (1991)
Nakano H, Kumagai N, Matsuzaki H, Kabuto C, Hongo H, Tetrahedron: Asymmetry, 8, 1391 (1997)
Beliczey J, Giffels G, Kragl U, Wandrey C, Tetrahedron: Asymmetry, 8, 1529 (1997)
Wilken J, Kossenjans M, Groger H, Martens J, Tetrahedron: Asymmetry, 8, 2007 (1997)
Soai K, Ookawa A, Kaba T, Ogawa K, J. Am. Chem. Soc., 109, 7111 (1987)
Jones GB, Heaton SB, Tetrahedron: Asymmetry, 4, 261 (1993)
Corey EJ, Hannon FJ, Tetrahedron Lett., 28, 5237 (1987)

[Referenced By]

[Related Articles]

[1] For reviews on Asymmetric Catalysis see: R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley-Interscience, New York (1993)

[2] Noyori R, Kitamura M, Angew. Chem.-Int. Edit., 30, 49 (1991)

[3] Soai K, Niwa S, Chem. Rev., references cited herein, 92, 833 (1992)

[4] Oguni N, Omi T, Tetrahedron Lett., 25, 2823 (1984)

[5] Kitamura M, Suga S, Kawai K, Noyori R, J. Am. Chem. Soc., 108, 6071 (1986)

[6] Kitamura M, Okada S, Suga S, Noyori R, J. Am. Chem. Soc., 111, 4028 (1989)

[7] Soai K, Yokoyama S, Hayasaka T, J. Org. Chem., 56, 4264 (1991)

[8] Nakano H, Kumagai N, Matsuzaki H, Kabuto C, Hongo H, Tetrahedron: Asymmetry, 8, 1391 (1997)

[9] Beliczey J, Giffels G, Kragl U, Wandrey C, Tetrahedron: Asymmetry, 8, 1529 (1997)

[10] Wilken J, Kossenjans M, Groger H, Martens J, Tetrahedron: Asymmetry, 8, 2007 (1997)

[11] Soai K, Ookawa A, Kaba T, Ogawa K, J. Am. Chem. Soc., 109, 7111 (1987)

[12] Jones GB, Heaton SB, Tetrahedron: Asymmetry, 4, 261 (1993)

[13] Corey EJ, Hannon FJ, Tetrahedron Lett., 28, 5237 (1987)