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. 2009 Jul 15;19(14):3955-8.
doi: 10.1016/j.bmcl.2009.03.012. Epub 2009 Mar 9.

Organocatalytic alpha-hydroxymethylation of cyclopentanone with aqueous formaldehyde: easy access to chiral delta-lactones

Nobuyuki Mase  1 , Azusa Inoue, Masaki Nishio, Kunihiko Takabe
Affiliations

Organocatalytic alpha-hydroxymethylation of cyclopentanone with aqueous formaldehyde: easy access to chiral delta-lactones

Nobuyuki Mase et al. Bioorg Med Chem Lett. .

Abstract

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.

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