Effects of reaction temperature and acyl group for lipase-catalyzed chiral binaphthol synthesis

Tetrahedron Letters

Volumn 47, Issue 28, 2006, Pages 4797-4801

  Aoyagi, Naoto ^a   Ogawa, Naomi ^a   Izumi, Taeko ^a  

^a YAMAGATA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 NAPHTHOL; 2,2' DIHYDROXY 1,1' BINAPHTHYL; O BUTYRYL 2,2' DIHYDROXY 1,1' BINAPHTHYL; O BUTYRYL 6,6' DIBROMO 2,2' DIHYDROXY 1,1' BINAPHTHYL; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ARTICLE; CANDIDA ANTARCTICA; CATALYSIS; CHEMICAL REACTION; CHIRALITY; ENANTIOMER; ENANTIOSELECTIVITY; HYDROLYSIS; REACTION ANALYSIS; SYNTHESIS; TEMPERATURE; TEMPERATURE SENSITIVITY;

CANDIDA ANTARCTICA;

EID: 33744828717     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.05.056     Document Type: Article

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35. +.
36. +).
37. The immobilized Candida antarctica lipase B (CALB) was provided by Novo Nordisk Co., Ltd. as CHIRAZYME L-2 (5 KU/g).
38. General procedure: CALB (40 mg) and n-butanol (0.672 mmol) were added to a solution of O-acyl binaphthol (±)-2 or (±)-3 (0.0672 mmol) and acetophenone (2.0 mg, standard substance) in solvent (2 mL) and the resulting mixture was stirred at 30-80 °C. The reaction conversion and enantiomeric excess were determined using HPLC (column, Daicel Chiralcel OG; mobile phase, hexane/2-propanol = 15:1; flow rate, 0.5 mL/min; UV detection at 254 nm). E values were calculated according to literature (see Ref. 31). Absolute configurations of the products were determined using HPLC (OG column) data of commercially available (R) and (S) BINOL.
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40. 20 +32.6 (c 1.0, THF)}.
41. Procedure of (R)-4 and (S)-5: CALB (40 mg) and alcohol (0.672 mmol) were added to a solution of (±)-5 (0.0672 mmol) and acetophenone (2.0 mg, standard substance) in toluene (2 mL) and the resulting mixture was stirred at 80 °C. The reaction conversion and enantiomeric excess were determined using HPLC (column, Daicel Chiralcel OD; mobile phase, hexane/2-propanol = 9:1; flow rate, 0.5 mL/min; UV detection at 254 nm). E values were calculated according to literature (see Ref. 31). Absolute configurations of the products were determined using HPLC (OD column) data of (R)-4 which was derived from commercially available (R)-BINOL.