| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1346796 | Tetrahedron: Asymmetry | 2011 | 8 Pages |
A ring closing metathesis reaction of dienes and a ring closing enyne metathesis reaction derived from allyl, homoallyl and homopropargyl alcohol backbones are described. 2-Heteroaryl substituted allyl, homoallyl and homopropargyl alcohols have been easily and efficiently resolved through enzymatic resolution with high ee (93–99%) and known stereochemistry. Enantiomerically enriched dienes derived from allyl and homoallyl alcohols afforded the corresponding enantiomerically enriched dihydrofuran and dihydropyran derivatives, respectively, with chemical yields which varied between 72% and 88%. On the other hand, enantiomerically enriched enynes derived from homoallyl and homopropargyl alcohols gave the corresponding optically active dihydropyrans with conjugated diene units with chemical yields between 70% and 80%. A subsequent Diels–Alder reaction of the dihydropyran derivatives with a diene unit with tetracyanoethylene resulted in the formation of a diastereomeric dihydroisochromene ring system as the sole product.
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(S)-(−)-2-(1-(Allyloxy)allyl)furanC10H12O2Ee = 99%[α]D28=-23.35 (c 1.0, CHCl3)Source of chirality: enzymatic resolutionAbsolute configuration: (1S)
(S)-(−)-2-(1-(Allyloxy)allyl)thiopheneC10H12OSEe = 97%[α]D26=-12.1 (c 0.5, CHCl3)Source of chirality: enzymatic resolutionAbsolute configuration: (1S)
(S)-(−)-2-(1-(Allyloxy)but-3-enyl)furanC11H14O2Ee = 99%[α]D29=-35.4 (c 0.5, CHCl3)Source of chirality: enzymatic resolutionAbsolute configuration: (1S)
(S)-(−)-2-(1-(Allyloxy)but-3-enyl)thiopheneC11H14OSEe = 99%[α]D29=-55.0 (c 1.0, CH2Cl2)Source of chirality: enzymatic resolutionAbsolute configuration: (1S)
(S)-(−)-2-(1-(Allyloxy)but-3-enyl)pyridineC12H15NOEe = 98%[α]D20=-69.8 (c 1.0, EtOH)Source of chirality: enzymatic resolutionAbsolute configuration: (1S)
(S)-(−)-2-(2,5-Dihydrofuran-2-yl)furanC8H8O2Ee = 99%[α]D22=-42.1 (c 1.0, CHCl3)Source of chirality: enzymatic resolutionAbsolute configuration: (1S)
(S)-(+)-2-(Thiophen-2-yl)-2,5-dihydrofuranC8H8OSEe = 97%[α]D15=+12.1 (c 1.0, CH2Cl2)Source of chirality: enzymatic resolutionAbsolute configuration: (1S)
(S)-(−)-2-(Furan-2-yl)-3,6-dihydro-2H-pyranC9H10O2Ee = 99%[α]D29=-77.2 (c 1.0, CH2Cl2)Source of chirality: enzymatic resolutionAbsolute configuration: (1S)
(S)-(−)-2-(Thiophen-2-yl)-3,6-dihydro-2H-pyranC9H10OSEe = 99%[α]D29=-17.8 (c 1.0, EtOH)Source of chirality: enzymatic resolutionAbsolute configuration: (1S)
(S)-(−)-2-(3,6-Dihydro-2H-pyran-2-yl)pyridineC10H11NOEe = 98%[α]D29=-18.8 (c 1.0, EtOH)Source of chirality: enzymatic resolutionAbsolute configuration: (1S)
(S)-(−)-2-(Furan-2-yl)-5-vinyl-3,6-dihydro-2H-pyranC11H12O2Ee = 99%[α]D29=-50.1 (c 1.0, CH2Cl2)Source of chirality: enzymatic resolutionAbsolute configuration: (2S)
(S)-(−)-2-(Thiophen-2-yl)-5-vinyl-3,6-dihydro-2H-pyranC11H12OSEe = 99%[α]D18=-107.1 (c 1.0, CH2Cl2)Source of chirality: enzymatic resolutionAbsolute configuration: (2S)
(S)-(−)-2-(Furan-2-yl)-4-vinyl-3,6-dihydro-2H-pyranC11H12O2Ee = 93%[α]D20=-17.9 (c 1.0, CH2Cl2)Source of chirality: enzymatic resolutionAbsolute configuration: (2S)
(S)-(−)-2-(Thiophen-2-yl)-4-vinyl-3,6-dihydro-2H-pyranC11H12OSEe = 99%[α]D22=-5.8 (c 1.0, CH2Cl2)Source of chirality: enzymatic resolutionAbsolute configuration: (2S)
(3S,4aR)-(+)-3-(Furan-2-yl)-4,4a-dihydro-1H-isochromene-5,5,6,6(3H,7H)-tetracarbonitrileC17H12N4O2Ee = 99%[α]D22=+98.1 (c 1.0, CH2Cl2)Source of chirality: enzymatic resolutionAbsolute configuration: (3S,4aR)
(3S,4aR)-(+)-3-(Thiophen-2-yl)-4,4a-dihydro-1H-isochromene-5,5,6,6(3H,7H)-tetracarbonitrileC17H12N4OSEe = 99%[α]D24=+85.2 (c 1.0, CH2Cl2)Source of chirality: enzymatic resolutionAbsolute configuration: (3S,4aR)
