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Z. Naturforsch.
69c, 170 – 180
(2014)
doi:10.5560/ZNC.2013-0128
Direct Asymmetric Aldol Reactions Catalyzed by Lipase from Porcine Pancreas
1 School of Chemistry and Chemical Engineering, Southwest University, Chongqing, 400715, China. E-mail:
guanzhi@swu.edu.cn and
heyh@swu.edu.cn
2 Luzhou Environmental Protection Monitoring Station, Luzhou, Sichuan, 646000, China
*Authors for correspondence and reprint requests
Received July 25, 2013 / January 26, 2014 / published online April 25, 2014
Porcine pancreas lipase type II (PPL II) exhibited unnatural catalytic activity in direct asymmetric aldol reactions between cyclic ketones and aromatic or heteroaromatic aldehydes in acetonitrile in the presence of phosphate buffer. A wide range of substrates was accepted by the enzyme to afford the corresponding aldol products in low to high yields (10%–98%), with moderate to excellent enantioselectivities (53%–94% ee, for anti-isomers) and low to moderate diastereoselectivities (48/52–87/13 dr, anti/syn). This methodology expands the application of PPL II, and it might be developed into a potentially valuable method for sustainable organic synthesis.
Key words: Aldol Reaction, Enantioselectivity, Lipase