Sharpless Asymmetric Dihydroxylation:: Effect of Alkene Structure on Rates and Selectivity

Alan C. Spivey ^[1] ; R. Hanson ^[1] ; N. Scorah ^[1] ; S. J. Thorpe ^[1]
1. [1] University of Sheffield
  
  University of Sheffield
  
  Reino Unido
Localización: Journal of chemical education, ISSN 0021-9584, Vol. 76, Nº 5 (May), 1999, págs. 655-655
Idioma: inglés
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Resumen
- Each student is assigned an alkene and performs three dihydroxylation reactions: one racemic and two enantioselective variants. The products are characterized by 1H NMR, IR, MS, [a]D20, and chiral chromatography (HPLC or GC). Comparison by the students of their results with those reported in the literature, particularly the extensive work of Sharpless, allows an exploration of the validity of Sharpless's mnemonic for predicting the stereochemical outcome of these reactions.