Molar scale synthesis of enantiopure stilbene oxide

Journal of Organic Chemistry

Volumn 61, Issue 18, 1996, Pages 6456-6457

  Chang, Han Ting ^a   Sharpless, K Barry ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000776037     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960718q     Document Type: Article

References (83)

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77. (a) The following control experiment was performed: a sample of stilbene oxide (3) (99% ee) was subjected to the reaction conditions overnight, whereupon ca. 90% of the epoxide had rearranged to deoxybenzoin, the major byproduct in the actual process. The enantiopurity of recovered 3 was reduced to 75% ee, and traces of the mesoepoxide and diphenylacetaldehyde were also detected,
78. 3. The reaction should be stopped when the epoxide to carbonate ratio is about 20:1.
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81. This silica gel filtration is very important. It removes the LiCl which otherwise causes decomposition of the epoxide during recrystallization from boiling MeOH.
82. The recrystallization is performed in an Erlenmeyer flask with a magnetic stir bar. The epoxide is added followed by the appropriate volume of MeOH and the mixture is heated to boiling while being stirred. The hot solution is then allowed to cool gradually to room temperature and the crystalline product is collected by filtration.
83. Epoxide 3 appears to be a racemic compound for which the enantiopure substance and the racemate have coincidentally the same melting point. Read, J.; Campbell, I. G. M. J. Chem. Soc. 1930, 2377.