Hydrogen Peroxide → (-)-cis-Myrtanol

反応式

B.C(SCCC(C)C)CC(C)C.B.COCCS[CH2:19][CH2:20][O:21]C.[CH3:23][C:24]1([CH3:32])[C@H:30]2[CH2:31][C@@H:25]1[CH2:26][CH2:27]C2=C.OO.[OH-].[Na+]>>[CH3:23][C:24]1([CH3:32])[C@H:30]2[CH2:31][C@@H:25]1[CH2:26][CH2:27][C@H:19]2[CH2:20][OH:21]

参加物

反応物 5

HCID 784Hydrogen Peroxide

HCID 14798Sodium Hydroxide

HCID 440967(-)-beta-Pinene

HCID 178419188HCID 178419188、化合物2 回

HCID 178419212HCID 178419212、化合物

生成物 1

HCID 11084102(-)-cis-Myrtanol収率 82%

実験手順

Hydroborations on a preparative scale were carried out with borane-diisoamyl sulfide and borane-bis(2-methoxyethyl) sulfide for illustrative purposes. Thus (-)-β-pinene (93% ee) was reacted with borane-diisoamyl sulfide and the organoborane intermediate was oxidized with standard 30% hydrogen peroxide and 3M sodium hydroxide used in excess to suppress oxidation of the sulfide. (-)-cis-Myrtanol was isolated by distillation in 82% yield and the sulfide was recovered.