| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1346542 | Tetrahedron: Asymmetry | 2016 | 9 Pages |
The optically active isomers of dimethyl octenone, which is used in citrus accords, and its analogs, were synthesized from a common chiral intermediate prepared by the lipase-catalyzed desymmetrization of prochiral diol. The results of an olfactory evaluation of the prepared isomers are also reported.
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(R)-3,6-Dimethyl-5-hepten-2-oneC9H16OEe = 95%[α]D24 = −27.6 (c 0.5, CHCl3)Source of chirality: lipase catalyzed reactionAbsolute configuration: (R)
(R)-4,7-Dimethyl-6-octen-3-oneC10H18OEe = 95%[α]D24 = −37.4 (c 1.1, CHCl3)Source of chirality: lipase catalyzed reactionAbsolute configuration: (R)
(R)-5,8-Dimethyl-7-nonen-4-oneC11H20OEe = 95%[α]D24 = −36.1 (c 0.5, CHCl3)Source of chirality: lipase catalyzed reactionAbsolute configuration: (R)
(R)-6,9-Dimethyl-8-decen-5-oneC12H22OEe = 95%[α]D24 = −34.6 (c 0.5, CHCl3)Source of chirality: lipase catalyzed reactionAbsolute configuration: (R)
(R)-2,5-Dimethyl-2-undecen-6-oneC13H24OEe = 95%[α]D24 = −32.3 (c 0.5, CHCl3)Source of chirality: lipase catalyzed reactionAbsolute configuration: (R)
