Enantiomeric resolution of asymmetric glycol by a lipase-catalyzed transesterification reaction

✍ Scribed by Akio Ichikawa

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 161 KB
• Volume: 11
• Category: Article
• ISSN: 0899-0042
• DOI: 10.1002/(sici)1520-636x(1999)11:4<338::aid-chir13>3.0.co;2-q

✦ Synopsis

The lipase catalyzed enantiomeric resolution of syn-glycol was carried out to confirm the sector method, which can determine the absolute configuration of anti-and syn-glycol from the 1 H-NMR spectra of bis-2-methoxy-2-trifluoromethyl-2phenylacetic acid (MTPA) esters. The lipase catalyzed transesterification reaction was most reactive at the C2 position (C2-OH) of (2R;3R)-2,3-octanediol. Both (2S;3S)-and (2R;3R)-2,3-octanediol were prepared using lipase. The 1 H-NMR spectra of their bis-(R)-MTPA esters agreed well with those prepared previously via mono-(R)-MTPA esters. The result suggests the retention of the Mosher plane in MTPA esters possessing a hydroxyl group at the ␤ position. The reaction rate and the stereoselectivity decreased at C2-OH with the addition of 18-crown-6.