Practical asymmetric synthesis of the herbicide (S)-indanofan via lipase-catalyzed kinetic resolution of a diol and stereoselective acid-catalyzed hydrolysis of a chiral epoxide.
Racemic indanofan [(+/-)-1] was efficiently converted to enantiopure (S)-indanofan [(S)-1] by a combination of enzymatic resolution and chemical inversion techniques. An additional important technique is the use of an o-xylene complex of a hemiketal (S)-3c as a precursor, which can be quantitatively converted to (S)-indanofan and easily purified by recrystallization from o-xylene.
Tanaka
Ken
K
Yokohama Research Center, Mitsubishi Chemical Corporation, 1000 Kamoshida-cho, Aoba-ku, Yokohama, Kanagawa 227-8502, Japan. 3200670@cc.m-kagaku.co.jp
Yoshida
Kenji
K
Sasaki
Chiduko
C
Osano
Yasuko T
YT
D002384:Catalysis; D002722:Chlorobenzenes / Q000138:chemical synthesis*; D018360:Crystallography, X-Ray; D004852:Epoxy Compounds / Q000737:chemistry; D006540:Herbicides / Q000138:chemical synthesis*; D006868:Hydrolysis; D007189:Indans / Q000138:chemical synthesis*; D008049:Lipase / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010407:Penicillium / Q000201:enzymology; D013237:Stereoisomerism; D014992:Xylenes / Q000737:chemistry
D002722:Chlorobenzenes; D004852:Epoxy Compounds; D006540:Herbicides; D007189:Indans; D014992:Xylenes; D008049:Lipase; C464480:indanofan