Enzymatic Hydrolysis and Selective Racemisation Reactions of α-Chloro Esters

Abstract

The kinetic resolution of α-chloro esters was effected with good selectivity using CLEC (Cross-Linked Enzyme Crystals) enzymes. The selective racemisation of α-chloro esters in the presence of α-chloro acids enabled a successful dynamic kinetic resolution reaction to be performed.

Key words

enzymes - kinetic resolution - asymmetric synthesis - racemisation

References

• 1a Enzyme Catalysis in Organic Synthesis   Vol. 1:  Drauz K. Waldmann H. VCH; Weinheim: 1995. 
• 1b Wong C.-H. Whitesides GM. Enzymes in Synthetic Organic Chemistry   Pergamon; Oxford: 1994. 
• 2a Pugniere M. Juan CS. Previero A. Tetrahedron Lett.  1990,  31:  4883 
• 2b Kim SB. Choi CY. Biotechnology Lett.  1995,  17:  1075 
• 2c Garcia MJ. Brieva R. Rebolledo F. Gotor V. Biotechnology Lett.  1991,  13:  867 
• 3a Bojarski J. Oxelbark J. Andersson C. Allenmark S. Chirality  1993,  5:  154 
• 3b Kirchner G. Scollar MP. Klibanov AM. J. Am. Chem. Soc.  1985,  107:  7072 
• 3c Jones MM. Williams JMJ. Chem. Commun.  1998,  2519 
• 4a Stecher H. Faber K. Synthesis  1997,  1 
• 4b Ward RS. Tetrahedron: Asymmetry  1995,  6:  1475 
• 4c El Gihani MT. Williams JMJ. Curr. Opin. Chem. Biol.  1999,  3:  11 
• 5 Pitaenen MT. Kohonen IO. Korvola JNJ. Tetrahedron  1981,  37:  529 
• 6 Slough GA. Tetrahedron Lett.  1990,  34:  6825 
• 7 Caddick S. Jenkins K. Chem. Soc. Rev.  1996,  447 
• 8 Koh K. Durst T. J. Org. Chem.  1994,  59:  4683 
• 9 Higgins SD. Thomas CB. J. Chem. Soc., Perkin Trans. 1  1983,  1483