Rhodium-phosphoramidite catalyzed alkene hydroacylation: mechanism and octaketide natural product synthesis

M von Delius, CM Le, VM Dong

Index: Von Delius, Max; Le, Christine M.; Dong, Vy M. Journal of the American Chemical Society, 2012 , vol. 134, # 36 p. 15022 - 15032

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Citation Number: 56

Abstract

We describe a method that allows salicylaldehyde derivatives to be coupled with a wide range of unactivated alkenes at catalyst loadings as low as 2 mol%. A chiral phosphoramidite ligand and the precise stoichiometry of heterogeneous base are key for high catalytic activity and linear regioselectivity. This protocol was applied in the atom-and step-economical synthesis of eight biologically active octaketide natural products, ...