Highly regioselective lipase-catalyzed acetylation and hydrolysis of acyclic α,α′-alkenediols and their diacetates

Tetrahedron Letters

Volumn 46, Issue 37, 2005, Pages 6293-6295

  Hisano, Takaya ^a   Onodera, Kotoko ^a   Toyabe, Yasuhiro ^a   Mase, Nobuyuki ^a   Yoda, Hidemi ^a   Takabe, Kunihiko ^a  

^a SHIZUOKA UNIVERSITY   (Japan)

Author keywords

Building block; Lipase catalyzed reaction; Regioselectivity

Indexed keywords

ACETOACETIC ACID; ALKENE DERIVATIVE; TRIACYLGLYCEROL LIPASE;

ACETYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; HYDROLYSIS KINETICS; PROTON NUCLEAR MAGNETIC RESONANCE; SCREENING; STEREOCHEMISTRY; WITTIG REACTION;

EID: 23744449040     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.07.039     Document Type: Article

References (12)

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11. Typical procedure (Table 2, entry 10): To a solution of the α,α′-alkenediols 2e (164 mg, 1.0 mmol, 1.0 equiv) and vinyl acetate (92 μL, 1.0 mmol, 1.0 equiv) in 1,4-dioxane (1.0 mL) was added Lipase AK (16 mg), and stirred for 4 h at 25°C. The reaction mixture was filtrated to remove the Lipase AK, concentrated to give the crude acetate. The crude product was purified by column chromatography (silica gel, hexane/AcOEt = 70/30) to give the monoacetates 3e (186 mg, 90%), the diacetate 4 e (12 mg, 5%) and the recovered diol 2e (8 mg, 5%).
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