| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1350558 | Tetrahedron: Asymmetry | 2007 | 7 Pages |
The preparation of three types of cyclic alkenols, (S)-2-cyclohexenol, (R)-2,5-dihydrobenzo[b]oxepin-5-ol, and (R)-5,6-dihydro-2H-benzo[b]oxocin-6-ol, has been accomplished in enantiomerically pure forms as model compounds using a combination of a lipase-catalyzed reaction and a ring closing olefin metathesis (RCM) reaction.
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(S)-Cyclohex-2-enyl 2-phenoxyacetateC14H16O3Ee = 99.6%[α]D25=-56.9 (c 0.9, CHCl3)Absolute configuration: (S)
(S)-Octa-1,7-dien-3-yl 2-phenoxyacetateC16H20O3Ee = 99.6%[α]D25=-11.9 (c 1.2, CHCl3)Absolute configuration: (S)
(S)-Octa-1,7-dien-3-yl acetateC10H16O2Ee = 97%[α]D23=-12.0 (c 1.12, CHCl3)Absolute configuration: (S)
(S)-1-(2-(Allyloxy)phenyl)prop-2-en-1-olC12H14O2Ee >99%[α]D22=-18.6 (c 1.0, CHCl3)Absolute configuration: (S)
(R)-1-(2-(Allyloxy)phenyl)allyl acetateC14H16O3Ee >99%[α]D22=+41.4 (c 1.0, CHCl3)Absolute configuration: (R)
(S)-1-(2-(Allyloxy)phenyl)but-3-en-1-olC13H16O2Ee = 32%[α]D25=-4.5 (c 1.0, CHCl3)Absolute configuration: (S)
(R)-1-(2-(Allyloxy)phenyl)but-3-enyl acetateC15H18O3Ee >99%[α]D22=+53.2 (c 1.0, CHCl3)Absolute configuration: (R)
(R,Z)-2,5-Dihydrobenzo[b]oxepin-5-yl acetateC12H12O3Ee >99%[α]D25=+3.4 (c 1.0, CHCl3)Absolute configuration: (R)
(R,Z)-5,6-Dihydro-2H-benzo[b]oxocin-6-yl acetateC13H14O3Ee >99%[α]D25=-7.5 (c 1.0, CHCl3)Absolute configuration: (R)
