| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1348451 | Tetrahedron: Asymmetry | 2006 | 6 Pages |
An intramolecular Pauson–Khand reaction of enynes derived from homoallyl and homopropargyl alcohols is described. 2-Furyl substituted homoallyl and homopropargyl alcohols are easily and efficiently resolved through enzymatic resolution in a high ee (93–99%) with a known stereochemistry. Each enantiomerically enriched enyne affords the conformationally most stable diastereomeric cyclopenta[c]pyran ring system.
Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide
(R)-(+)-1-(Furan-2-yl)but-3-ynyl acetateC10H10O3Ee = 90%[α]D29=+54.6 (c 4.0, MeOH)Source of chirality: enzymatic resolutionAbsolute configuration: (1R)
(S)-(−)-2-(1-(prop-2-ynyloxy)but-3-enyl)furanC11H12O2Ee = 99%[α]D20=-67.5 (c 2.7, CH2Cl2)Source of chirality: enzymatic resolutionAbsolute configuration: (1S)
(S)-(−)-2-(1-allyloxy)but-3-ynyl)furanC11H12O2Ee = 93%[α]D20=-8.5 (c 0.5, MeOH)Source of chirality: enzymatic resolutionAbsolute configuration: (1S)
(3S,4aR)-(+)-3-(Furan-2-yl)-3,4,4a,5-tetrahydrocyclopenta[c]pyran-6(1H)-oneC12H12O3Ee = 99%[α]D20=+35.5 (c 1.7, CH2Cl2)Source of chirality: enzymatic resolutionAbsolute configuration: (3S,4aR)
(3S,7aR)-(+)-3-(Furan-2-yl)-3,4,7,7a-tetrahydrocyclopenta[c]pyran-6(1H)-oneC12H12O3Ee = 93%[α]D20=+99.1 (c 3.6, MeOH)Source of chirality: enzymatic resolutionAbsolute configuration: (3S,7aR)
