Lipase-supported Preparation of Optically Active 2-Amino Alcohols of Biological Interest

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

Journal of Industrial and Engineering Chemistry, Vol.3, No.3, 182-184, September, 1997

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

Department of Chemical Engineering, Inha University, Inchon 402-571, Korea

Transesterification of racemic N-acetylated 2-amino alcohols with vinyl acetate was investigated in the presence of inexpensive commercial porcine pancreatic lipase. The enzymatic kinetic resolution occurred with high reactivity and enantioselectivity to give optically pure N,O-diacetylate and N-monoacetylate. This result clearly indicates that the biocatalytic route can be efficiently used in the preparation of enantiopure 2-amino alcohol.

[References]

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[Related Articles]

[1] Whitesides GM, Wong CH, Angew. Chem.-Int. Edit., 24, 617 (1985)

[2] Jones JB, Tetrahedron, 42, 3351 (1986)

[3] Wong CH, Science, 244, 1145 (1989)

[4] Klibanov AM, Accounts Chem. Res., 23, 114 (1990)

[5] Barth S, Effenberger F, Tetrahedron: Asymmetry, 4, 823 (1993)

[6] Caetan G, Kazlauskas RJ, Tetrahedron: Asymmetry, 4, 1995 (1993)

[7] Kirchner G, Scollar MP, Klibanov AM, J. Am. Chem. Soc., 109, 7072 (1987)

[8] Kitaguchi H, Fitzpatrick PA, Huber JE, Klibanov AM, J. Am. Chem. Soc., 111, 3094 (1989)

[9] Cambou B, Klibanov AM, J. Am. Chem. Soc., 106, 2687 (1984)

[10] Ojima I, Kato K, Nakahashi K, Fuchikami T, Fujita M, J. Org. Chem., 54, 4511 (1989)

[11] Chenault HK, Dahmer J, Whitesides GM, J. Am. Chem. Soc., 111, 6354 (1989)

[12] Jurczak J, Golebiowski A, Chem. Rev., 89, 149 (1989)

[13] Nakanishi K, Goto T, Ito S, Natori S, Nozoe S, Natural Products Chemistry, Vol. 3, Oxford University Press, Oxford (1989)

[14] Wilkinson RG, Cantrall MB, Shepherd RG, J. Med. Chem., 5, 835 (1962)

[15] Gotor V, Brieva R, Rebolledo F, J. Chem. Soc.-Chem. Commun., 957 (1988)

[16] Francalanci F, Cesti P, Cabri W, Bianchi D, Martinengo T, Foa M, J. Org. Chem., 52, 5079 (1987)