Direct Catalytic Asymmetric Aldol Reaction of α‐Alkoxyamides to α‐Fluorinated Ketones

α‐Oxygen functionalized amides found its particular utility as enolate surrogates for direct aldol coupling with α‐fluorinated ketones in a catalytic manner. Likely involvement of open transition state allows access to both syn‐ and anti‐aldol adducts with high enantioselectivity by judicious choice of chiral ligands. The broad scopes of alkoxy substituents of amides, and aryl and fluoroalkyl groups of ketones were leveraged by divergent diastereoselectivity to deliver a range of enantioenriched fluorinated 1,2‐dihydroxy carboxylic acid derivatives. The amide moiety of the aldol adduct was transformed into a variety of functional groups without requiring protection of the tertiary alcohol, showcasing the synthetic utility of the present asymmetric aldol protocol.

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