A lipase catalyzed condensation reaction with a tricyclic diketone: yet another example of biocatalytic promiscuity

作者：Majumder Abir B; Ramesh Namakkal G^*; Gupta Munishwar N

来源：Tetrahedron Letters, 2009, 50(37): 5190-5193.

DOI：10.1016/j.tetlet.2009.06.108

• Aldol condensation
• Candida antarctica lipase B
• Non-aqueous media
• Tricyclic 1,3-diketone
• Vinyl acetate

Novozym 435 (a commercially available immobilized form of Candida antarctica lipase B) was found to catalyze a condensation reaction of 5-hydroxy-endo-tricyclo[5.2.1.0(2,6)]deca-4,8-dien-3-one with acetaldehyde (enzymatically produced from vinyl acetate in situ) under low water conditions, in presence of 10% organic co-solvent (N,N-dimethyl formamide or pyridine), to form a bis-adduct. Even though the condensation reaction occurred with pyridine (acting as a base catalyst) in the presence of acetaldehyde and in the absence of enzyme, the reaction was very slow as compared to the enzymatic process. Thus, while the non-enzymatic process took 4 days to achieve 100% conversion; in presence of enzyme it was possible within 4 h.

• 出版日期2009-9-16