تفاعل #694173

معادلة التفاعل

2-Benzhydryl-oxirane

toluene

acetic acid

→

(2S)-3,3-diphenyl-propane-1,2-diol

(2R)-2-benzhydryl-oxirane

المذيبات

water

H2O

ظروف التفاعل

المعالجة

1. 1
   أخرىThe solvent was removed in vacuo
2. 2
   أخرىthe residue was dried
3. 3
   workup.STIRRINGstirred
4. 4
   درجة الحرارةthe mixture was then cooled by means of an ice-bath
5. 5
   أخرىthe ice bath was removed
6. 6
   workup.STIRRINGthe reaction mixture was stirred at room temperature for 72 h
7. 7
   أخرىCompounds were separated via flash chromatography on silica gel column

الإجراء التجريبي

A mixture of (R,R)-(−)-N,N′-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexane diaminocobalt (II) (0.22 g, 0.37 mmol, 0.8%), toluene (5 ml), and acetic acid (0.044 g, 0.74 mmol) was stirred for 1 h at room temperature. The solvent was removed in vacuo and the residue was dried. 2-Benzhydryl-oxirane (9.6 g, 45.7 mmol) was added in one portion and stirred, the mixture was then cooled by means of an ice-bath. H2O (0.58 g, 32 mmol) was slowly added over a 30-min period. After water addition, the ice bath was removed and the reaction mixture was stirred at room temperature for 72 h. Compounds were separated via flash chromatography on silica gel column to give (2R)-2-benzhydryl-oxirane (23a) 4.5 g ([α]D=(+)9.58, c=1, MeOH) and (2S)-3,3-diphenyl-propane-1,2-diol 24 3.53 g ([α]D=(+)48, c-=1, MeOH, ee=97%). The proton and carbon NMR data of (2R)-2-benzhydryl-oxirane was identical to the racemate 2-benzhydryl-oxirane.

المصدر