Journal
ORGANIC CHEMISTRY FRONTIERS
Volume 10, Issue 6, Pages 1564-1569Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2qo01912d
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A method for desymmetrizing asymmetric ring expansion of 4-substituted cyclohexanones with alpha-diazomethylphosphonates catalyzed by a chiral boron Lewis acid has been developed. The method affords beta-ketophosphonate compounds bearing a stereogenic center at the alpha-position in up to 80% yields, 86% ee, and >20 : 1 dr. The obtained products can be further derivatized, demonstrating the synthetic potential of this reaction.
A method for desymmetrizing asymmetric ring expansion of 4-substituted cyclohexanones with alpha-diazomethylphosphonates catalyzed by a chiral boron Lewis acid has been developed. The method affords beta-ketophosphonate compounds bearing a stereogenic center at the alpha-position in up to 80% yields, 86% ee, and >20 : 1 dr. The obtained products can be further derivatized, demonstrating the synthetic potential of this reaction.
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