| Autor: |
Krisztián Bogár, Belén Martín-Matute, Jan-E. Bäckvall |
| Jazyk: |
angličtina |
| Rok vydání: |
2007 |
| Předmět: |
|
| Zdroj: |
Beilstein Journal of Organic Chemistry, Vol 3, Iss 1, p 50 (2007) |
| Druh dokumentu: |
article |
| ISSN: |
1860-5397 |
| DOI: |
10.1186/1860-5397-3-50 |
| Popis: |
The scale-up of the ruthenium- and enzyme-catalyzed dynamic kinetic resolution (DKR) of (rac)-1-phenylethanol (2) is addressed. The immobilized lipase Candida antarctica lipase B (CALB) was employed for the resolution, which shows high enantioselectivity in the transesterification. The ruthenium catalyst used, (η 5-C5Ph5)RuCl(CO)2 1, was shown to possess very high reactivity in the "in situ" redox racemization of 1-phenylethanol (2) in the presence of the immobilized enzyme, and could be used in 0.05 mol% with high efficiency. Commercially available isopropenyl acetate was employed as acylating agent in the lipase-catalyzed transesterifications, which makes the purification of the product very easy. In a successful large-scale DKR of 2, with 0.05 mol% of 1, (R)-1-phenylethanol acetate (3) was obtained in 159 g (97% yield) in excellent enantiomeric excess (99.8% ee). |
| Databáze: |
Directory of Open Access Journals |
| Externí odkaz: |
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