Iodine → HCID 57212103, compound

Participants

Reaction Conditions

Reaction Steps

1.67 g of of (Z)-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-prop-2-en-1-ol were dissolved in 36 ml of CH2Cl2. At 0° C. 7.62 ml of Et2Zn-solution (1M[hexane]) was added, followed 15 min. later by 1.33 ml of L-(+)-diethyl tartrate, dissolved in 18 ml of CH2 Cl2. Stirring was continued for 45 min. The reaction flask was then cooled to -22° C. and another portion of 13.8 ml of Et2 Zn-solution (1M[hexane]) was added, followed by 2.23 ml of CH2 I2. The reaction flask was allowed to reach +18° C. during 16 h. After quenching with crushed ice/NH4CI-solution, the mixture was extracted with EtOEt, washed with dil. HCI and H2O, dried over Na2SO4 and evaporated to dryness. Flash chromatography (silica gel, hexane/AcOEt=87/13) yielded 1.057 g of (1R,2S)-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-cyclopropylmethanol, 99% pure according to GC. The absolute configuration was assigned in analogy to Chemistry Letters 1992, 61, but not rigorously proven; the optical purity was determined at the next stage.

Provenance & Evidence