Journal
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
Volume 19, Issue 14, Pages 3955-3958Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmcl.2009.03.012
Keywords
Organocatalysis; Chiral lactone; Jasmine lactone; Aldol reaction
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Funding
- Japan Society for the Promotion of Science
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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. (C) 2009 Elsevier Ltd. All rights reserved.
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