The enhancement of enantioselectivities for lipase-catalyzed reactions by using carbamates

Tetrahedron Letters

Volumn 39, Issue 48, 1998, Pages 8881-8884

  Lin, Gialih ^a   Lin, Wen Yuan ^a   Shieh, Chuen Tzwu ^a  

^a NATIONAL CHUNG HSING UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBAMIC ACID DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONCENTRATION (PARAMETERS); ENANTIOMER; STRUCTURE ACTIVITY RELATION;

SUIDAE;

EID: 0032569924     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02021-8     Document Type: Article

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22. 22. General procedures: a) Synthesis of Carbamates 1-8. Carbamates 1-8 were prepared from the condensation of the corresponding alcohol with isocyanate in the presence of pyridine (70-90% yield).
23. b) PPL-catalyzed resolution of 1-indanylacetate in the presence ofcarbamates 1. To a t-butyl methyl ether (15 mL) solution of carbamate 1 (37.6 μmol), PPL (4 g, Sigma L0382) was added and the resulting mixture was shaken at 37 °C for 24 h. To the above mixture, rac-9 (3.76 mmol) and water (0.38 mol) were added and the reaction mixture was shaken at 37 °C for 24 h. The resulting mixtures were concentrated and separated by MPLC (hexane/ethyl acetate, 4/1, v/v).
24. c) Figure 1. To a t-butyl methyl ether (20 mL) solution of varying concentration of carbamate 2, PPL (4 g) was added. The resulting mixture was shaken at 37 °C for 24 h (pre-incubation). To this mixture, rac-10 (3.76 mmol) and vinyl butyrate (4.5 mmol) were added. The reaction mixture was shaken for another 24 h at 37 °C.
25. d) Figure 2. All procedures were similar to that of c) except the pre-incubation time.
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