New Chiral Catalyst for Asymmetric Alkylation of Aldehydes with Diethylzinc

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

Journal of Industrial and Engineering Chemistry, Vol.3, No.1, 37-38, March, 1997

Sang-Han Kim, Sum-Jin Ahn, Sung-Taik Chung, and Myung-Jong Jin

Department of Chemical Engineering, Inha University, Incheon 402-751, Korea

Asymmetric alkylation of aromatic aldehydes with diethylzinc in the presence of catalytic amount of chiral thiazolidines derived from L-cysteine ethyl ester afforded the corresponding optically active secondary alcohols.

[References]

For reviews on Asymmetric Catalysis see: R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley-Interscience, New York (1993)
Brunner H, Becker R, Riepl G, Organometallics, 3, 1354 (1984)
Oguni N, Omi T, Tetrahedron Lett., 25, 2823 (1984)
Corey EJ, Hannon FJ, Tetrahedron Lett., 28, 5233 (1987)
Corey EJ, Hannon FJ, Tetrahedron Lett., 28, 5237 (1987)
Smaardijk A, Wynberg H, J. Org. Chem., 52, 135 (1987)
Yokoyama S, Ebihara K, Hayasaka T, J. Chem. Soc.-Chem. Commun., 1690 (1987)
Soai K, Niwa S, Yamada Y, Inoue H, Tetrahedron Lett., 28, 4841 (1987)
Kitamura M, Okada S, Suga S, Noyori R, J. Am. Chem. Soc., 111, 4028 (1989)
Itsuno S, Sakurai Y, Ito K, Maruyama T, Nakahama S, Frechet JMJ, J. Org. Chem., 55, 304 (1990)
Corey EJ, Yuen P, Hannon FJ, Wierda DA, J. Org. Chem., 55, 784 (1990)
Noyori R, Kitamura M, Angew. Chem.-Int. Edit., 30, 49 (1991)
Soai K, Yokoyama S, Hayasaka T, J. Org. Chem., 56, 4264 (1991)
William JMJ, Allen JV, Frost CG, Tetrahedron: Asymmetry, 4, 649 (1993)
Natsumoto Y, Ohno SL, Hayashi T, Tetrahedron: Asymmetry, 4, 1763 (1993)
Noyori R, Kitamura M, Angew. Chem.-Int. Edit., 30, 49 (1991)
Soai K, Niwa S, Chem. Rev., 92, 833 (1993)
Jones BG, Heaton BS, Tetrahedron: Asymmetry, 4, 261 (1993)

[Related Articles]

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

[2] Brunner H, Becker R, Riepl G, Organometallics, 3, 1354 (1984)

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

[4] Corey EJ, Hannon FJ, Tetrahedron Lett., 28, 5233 (1987)

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

[6] Smaardijk A, Wynberg H, J. Org. Chem., 52, 135 (1987)

[7] Yokoyama S, Ebihara K, Hayasaka T, J. Chem. Soc.-Chem. Commun., 1690 (1987)

[8] Soai K, Niwa S, Yamada Y, Inoue H, Tetrahedron Lett., 28, 4841 (1987)

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

[10] Itsuno S, Sakurai Y, Ito K, Maruyama T, Nakahama S, Frechet JMJ, J. Org. Chem., 55, 304 (1990)

[11] Corey EJ, Yuen P, Hannon FJ, Wierda DA, J. Org. Chem., 55, 784 (1990)

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

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

[14] William JMJ, Allen JV, Frost CG, Tetrahedron: Asymmetry, 4, 649 (1993)

[15] Natsumoto Y, Ohno SL, Hayashi T, Tetrahedron: Asymmetry, 4, 1763 (1993)

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

[17] Soai K, Niwa S, Chem. Rev., 92, 833 (1993)

[18] Jones BG, Heaton BS, Tetrahedron: Asymmetry, 4, 261 (1993)