170501-87-8Relevant academic research and scientific papers
Lipase promoted asymmetric trans-esterification of 4-alkyl-, 3-alkyl- and 3,4-dialkyloxetan-2-ones with ring-opening
Sakai, Naoko,Ageishi, Satoru,Isobe, Hiroshi,Hayashi, Yoshiyuki,Yamamoto, Yukio
, p. 71 - 78 (2007/10/03)
Kinetic resolution of(+/-)-4-substituted [(+/-)-1], 3-substituted [(+/-)-4] and 3,4-disubstituted oxetan-2-ones [(+/-)-7] was effected by the action of lipases in organic solvents. The substrates (+/-)-1, (+/-)-4 and (+/-)-7 were prepared by [2 + 2] cycloaddition of aldehydes with ketene, intramolecular substitution of 3-bromoalkanoic acids and the Adam's cyclization of anti- and syn-3-hydroxyalkanoic acids, respectively. Lipase PS exhibited good activity towards all the oxetanones and was employed for the resolution experiments except with (+/-)-4-methyloxetan-2-one (+/-)-1a for which PPL was used. The stereoselectivity was satisfactory for obtaining oxetan-2-ones of high ee's except for a few cases. The configuration of new compounds was established by chemical correlation and CD spectroscopy.
Lipase-promoted asymmetric transesterification of 4-alkyloxetan-2-ones with ring-opening
Koichi, Yota,Suginaka, Kaoru,Yamamoto, Yukio
, p. 1645 - 1646 (2007/10/02)
Lipase-catalysed reaction of (+/-)-4-alkyloxetan-2-ones 1a-c with benzyl alcohol gave (R)-1a (R=Me) (36percent, 96percent ee) and benzyl (S)-3-hydroxybutanoate 2a (51percent, 85percent ee), (R)-1b (R=Pr) (42percent, 75percent ee) and benzyl (S)-3-hydroxyhexanoate 2b (45percent, 69percent ee) and (S)-1c (R=Pr-i, 41percent, 95percent ee) and benzyl (R)-3-hydroxy-4-methylpentanoate 2c (43percent, 90percent ee), respectively.
