| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1346019 | Tetrahedron: Asymmetry | 2005 | 5 Pages |
Two routes for the synthesis of enantiopure cycloheptenones, intermediates for perhydroazulene terpenoids, have been developed. They feature totally regioselective Tiffeneau–Demjanov and Nozaki ring expansion reactions of (R)-(−)-carvone.
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(1R,5R)-5-Isopropenyl-2-methyl-1-trimethylsilanyloxy-cyclohex-2-enecarbonitrileC14H23NOSi[α]D25=-124 (c 2.9, CHCl3)Source of chirality: (R)-(−)-carvoneAbsolute configuration (1R,5R)
(1R,5R)-1-Aminomethyl-5-isopropenyl-2-methyl-cyclohex-2-enol-1C11H19NO[α]D25=-92.2 (c 2.0, CHCl3)Source of chirality: (R)-(−)-carvoneAbsolute configuration (1R,5R)
(R)-6-Isopropenyl-3-methyl-cyclohept-3-enoneC11H16O[α]D25=+30 (c 0.26, CHCl3)Source of chirality: (R)-(−)-carvoneAbsolute configuration (R)
(R)-6-Isopropenyl-3-methyl-cyclohept-2-enoneC11H16O[α]D25=+49.0 (c 0.13, CHCl3)Source of chirality: (R)-(−)-carvoneAbsolute configuration (R)
(1R,5R)-1-(dibromomethyl)-5-isopropenyl-2-methylcyclohex-2-enol-1C11H16Br2O[α]D25=-65.8 (c 1.5, CHCl3)Source of chirality: (R)-(−)-carvoneAbsolute configuration (1R,5R)
(1S,5R)-1-(Dibromomethyl)-5-isopropenyl-2-methylcyclohex-2-enol-1C11H16Br2O[α]D25=-20.4 (c 1.2, CHCl3)Source of chirality: (R)-(−)-carvoneAbsolute configuration (1S,5R)
