Preparation of optically active α-hydroxy ketone derivatives by Enzyme-Mediated Hydrolysis of Enol Esters

✍ Scribed by Kazutsugu Matsumoto; Natsuko Suzuki; Hiromichi Ohta

• Publisher: Elsevier Science
• Year: 1990
• Tongue: French
• Weight: 257 KB
• Volume: 31
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)97267-8

✦ Synopsis

A new method of preparation of optically active a-hydroxy ketone derivatives has been developed. Incubation of (Z)-3-propionyloxy4-benzyloxy-2-pentcne (la) with lipasc OF gave optically pure (R)-cnol propionatc la, which in bun was converted without raccmization to @)-ketone 2a by the aid ofLiAlH4.

Optically active a-hydroxy ketone derivatives are important intermediates in asymmetric organic synthesis. Naturally occur@ a-hydroxy and amino acids are important chiral sources for such class of compounds, but they are hardly sufficient to supply for a variety of compounds.

In the previous papers, we have reported a new type of enzyme-mediated kinetic resolution via hydrolysis of enol esters (Scheme 1).1) Enzymatic hydrolysis of enol esters directly affords optically active ketone derivatives when the enzyme system distinguishes the configuration of a-position. In this paper, we applied this methodology to the preparation of optically active a-hydroxy ketone