A novel strategy for the convergent synthesis of 1,3,5,...-polyols: Enone formation, asymmetric dihydroxylation, reductive cleavage, hydride addition

作者：Korber K; Risch P; Bruckner R^*

来源：Synlett, 2005, (19): 2905-2910.

DOI：10.1055/s-2005-921915

• defunctionalization
• 1,3-diol
• Horner-Wadsworth-Emmons olefination
• beta-hydroxy ketones
• samarium iodide
• alpha,beta-unsaturated ketones

Asymmetric dihydroxylation of alpha, beta-unsaturated ketones provided a,p-dihydroxyketones with up to 100% ee. The C-alpha -O bond of these intermediates or their bis-TMS ethers, acetonides, phenylborates or orthoformiates was cleaved with SmI2, affording beta-hydroxyketones. The latter can be reduced to furnishsyn- or anticonfigured 1,3-diols of any desired configuration.