The application of a mechanistic model leads to the extension of the Sharpless asymmetric dihydroxylation to allylic 4-methoxybenzoates and conformationally related …

EJ Corey, A Guzman-Perez…

Index: Corey; Guzman-Perez, Angel; Noe, Mark C. Journal of the American Chemical Society, 1995 , vol. 117, # 44 p. 10805 - 10816

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Citation Number: 145

Abstract

Abstract: The scope and utility of the Sharpless asymmetric dihydroxylation has been expanded to include the use of allylic 4-methoxybenzoates as precursors of a wide variety of substituted chiral glycerol derivatives. The allylic 4-methoxybenzoyl group was found to be superior to other allylic alcohol protecting groups with respect to both yield and enantiomeric purity of the product. For example, asymmetric dihydroxylation of allyl 4-methoxybenzoate ...