H

4158

Figure 16: Temperature effect where lowering the temperature decreases the enantioselectivity.

6. LIPASE-CATALYZED RESOLUTION OF PRIMARY ALCOHOLS: PROMISING CANDIDATES FOR THE "LOW-TEMPERATURE METHOD"

Examples of the lipase-catalyzed resolution of primary alcohols are listed in Fig. 17.63-126 They usually give low enantioselectivity because of mechanistic reasons, and no effective method for improving the enantioselectivity is available. One of the purposes of this book is to create new ideas and possibilities in this field. The "low-temperature method" is a promising one to improve the enantioselectivity of these alcohols.

Figure 17: Example of lipase-catalyzed resolution of primary alcohols [lit.].
•Oh

ch2oh ch3

(ch2)9othp

N CH2OH Ac

Me 2

i-Pr 29 Lipase YS

CRL E= 104

Amano P

Figure 17: Continued.

7. CONCLUSION

Here, the temperature effect is discussed from the aspect of synthetic utility. Temperature control of enantioselectivity, i.e., the "low-temperature method", is simple and now practically acceptable method. The phenomenon is based on the theory of physical organic chemistry and will be studied further for understanding the enzymatic reaction as organic reaction.

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chiral 1,2-diols

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Future Directions in Biocatalysis Edited by Tomoko Matsuda © 2007 Elsevier B.V. All rights reserved.

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