Organocatalytic α-hydroxymethylation of cyclopentanone with aqueous formaldehyde: Easy access to chiral δ-lactones

Optically active lactones are important synthons in perfume and aroma manufacturing. Therefore, developments of efficient asymmetric syntheses are desired. Organocatalytic asymmetric α-hydroxymethylations of cyclopentanone with aqueous formaldehyde have been developed, to furnish the corresponding α-(hydroxymethyl)cyclopentanone with high enantioselectivity. Further chemical transformation of α-(hydroxymethyl)cyclopentanone gave the key intermediate for jasmine lactone, which is widely found in fruits and flowers.

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