Asymmetric Dihydroxylation of Esters and Amides of Methacrylic, Tiglic, and Angelic Acid: No Exception to the Sharpless Mnemonic!

作者：Weber Fabian; Brueckner Reinhard

来源：European Journal of Organic Chemistry, 2015, 2015(11): 2428-2449.

DOI：10.1002/ejoc.201403622

• Asymmetric catalysis
• Configuration determination
• Dihydroxylation
• 1,2-Diols
• Enantioselectivity
• Oxidation

Literature findings on the facial selectivity of the Sharpless asymmetric dihydroxylation (SAD) of isobutyl angelate are contradictory and partly in conflict with the Sharpless mnemonic. We systematically screened the SAD of esters and amides of angelic, tiglic, and methacrylic acid. Enantiocontrol arose in 14 of the 15 reactions, culminating at 99% ee for the Weinreb amide of tiglic acid. The absolute configurations of all the nonracemic products were established by (stereo)chemical correlations. Without exception, they conform to the Sharpless mnemonic.

• 出版日期2015-4