155682-86-3Relevant academic research and scientific papers
Enantioselective synthesis of (-)-γ-jasmolactone
Missio,Comasseto
, p. 4609 - 4615 (2000)
The title compound was prepared in seven steps starting from the commercially available 4-ketopimelic acid. The key step features an enantioselective lactonization promoted by PPL.
A short enantioselective synthesis of (R)-(+)-γ-jasmolactone
Clososki, Giuliano C.,Missio, Lauri J.,Comasseto, Joao V.
, p. 2371 - 2377 (2004)
(R)-(+)-γ-Jasmolactone (1b) was synthesized in 92%ee in two steps, starting from the easily prepared (S)-(-)-3-(5-oxo-tetrahydro-furan-2-yl)- propionic acid benzyl ester (2). The key step features an inversion of configuration of the stereogenic center.
Combination of novozym 435-catalyzed hydrolysis and mitsunobu reaction for production of (r)γ-lactones
Shimotori, Yasutaka,Miyakoshi, Tetsuo
experimental part, p. 1607 - 1613 (2010/06/21)
Chiral-lactones of both enantiomers were synthesized with more than 90% optical purities. The key step was Novozym 435-catalyzed hydrolysis of racemic N-benzyl-4-acetoxyalkylamides. Additionally, because (R)-γ-lactones are predominant in apricot, mango, peach, passion fruit, and strawberry, synthesis was attempted using only one enantiomer selectively. The (R)-enantimer was synthesized with more than 80% total yield and more than 90% optical purity by a combination of Novozym 435-catalyzed hydrolysis and the Mitsunobu reaction. Copyright
Facile synthesis of optically active γ-lactones via lipase-catalyzed reaction of 4-substituted 4-hydroxybutyramides
Matsumura, Yasufumi,Endo, Teruko,Chiba, Mitsuo,Fukawa, Hidemichi,Terao, Yoshiyasu
, p. 304 - 305 (2007/10/03)
Lipase-catalyzed transesterification of racemic 4-substituted 4- hydroxybutyramides with succinic anhydride proceeded enantioselectively to afford (S)-succinic acid monoester and unreacted (R)-4-hydroxybutyramide derivative, which were separated easily by
