Asymmetric synthesis of homoisoflavanone using lipase-catalyzed reaction

Heterocycles

Volumn 65, Issue 4, 2005, Pages 761-765

  Kawasaki, Masashi ^a   Toyooka, Naoki ^b   Matsui, Yoshinori ^c   Tanaka, Akira ^c   Goto, Michimasa ^d   Kakuda, Hiroko ^b   Kawabata, Shigeki ^a   Kometani, Tadashi ^d  

^a TOYAMA PREFECTURAL UNIVERSITY   (Japan)

^b UNIVERSITY OF TOYAMA   (Japan)

^c National Institute of Technology Kure College   (Japan)

^d Toyama National College of Technology   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33747114692     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-05-10347     Document Type: Article

References (38)

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31. The yields of the unreacted diol (2) and the diacetate (3) produced from monoacetate (4) measuredby GC analysis were about 0.7% and about 0.2%, respectively. We did not isolate them.
32. Determined by HPLC analysis on Chiralcel OB-H, hexane:2-propanol=7:1 (v/v), flow rate=0.5ml/min. Retention times: (S)-4, t=17 min; (R)-4, t=19 min.
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34. 7b
35. Determined by HPLC analysis on Chiralcel OB-H, hexane:2-propanol=20:1 (v/v), flow rate=0.5 ml/min. Retention times: (S)-8, t=28 min; (R)-8, t=32 min.
36. The yields of the unreacted diacetate (3) and the diol (2) produced from monoacetate (4) measuredby GC analysis were about 27% and about 32%, respectively.We did not isolate them.
37. Although 3 was also subjected to hydrolysis with other lipases, satisfactory results for the ee values of (S)-4 could not be obtained. Hydrolysis of 3 with Lipase ALC (Meito) yielded (S)-4 in 82% ee, while with Lipase PPL (Amano) did (R)-4 in 64% ee.
38. Mori et al also reported the conversion of 3 into (S)-4 by other lipases. However, they could not obtain (S)-4 in high ee. Mori K., Chiba N. Liebigs Ann. Chem. (1989) 957