Organocatalytic alpha-hydroxymethylation of cyclopentanone with aqueous formaldehyde: easy access to chiral delta-lactones.
Optically active lactones are important synthons in perfume and aroma manufacturing. Therefore, developments of efficient asymmetric syntheses are desired. Organocatalytic asymmetric alpha-hydroxymethylations of cyclopentanone with aqueous formaldehyde have been developed, to furnish the corresponding alpha-(hydroxymethyl)cyclopentanone with high enantioselectivity. Further chemical transformation of alpha-(hydroxymethyl)cyclopentanone gave the key intermediate for jasmine lactone, which is widely found in fruits and flowers.
Mase
Nobuyuki
N
Department of Molecular Science, Faculty of Engineering, Shizuoka University, Hamamatsu, Japan.
Inoue
Azusa
A
Nishio
Masaki
M
Takabe
Kunihiko
K