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Asymmetric Synthesis of ?-Amino Amides by Catalytic Enantioconvergent 2-Aza-Cope Rearrangement.

ABSTRACT: Dynamic kinetic resolutions of ?-stereogenic-?-formyl amides in asymmetric 2-aza-Cope rearrangements are described. Chiral phosphoric acids catalyze this rare example of a non-hydrogenative DKR of a ?-oxo acid derivative. The [3,3]-rearrangement occurs with high diastereo- and enantiocontrol, forming ?-imino amides that can be deprotected to the primary ?-amino amide or reduced to the corresponding diamine.

SUBMITTER: Goodman CG

PROVIDER: S-EPMC4661081 | biostudies-literature | 2015 Nov

REPOSITORIES: biostudies-literature

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Asymmetric Synthesis of β-Amino Amides by Catalytic Enantioconvergent 2-Aza-Cope Rearrangement.

Goodman C Guy CG Johnson Jeffrey S JS

Journal of the American Chemical Society 20151112 46

Dynamic kinetic resolutions of α-stereogenic-β-formyl amides in asymmetric 2-aza-Cope rearrangements are described. Chiral phosphoric acids catalyze this rare example of a non-hydrogenative DKR of a β-oxo acid derivative. The [3,3]-rearrangement occurs with high diastereo- and enantiocontrol, forming β-imino amides that can be deprotected to the primary β-amino amide or reduced to the corresponding diamine. ...[more]

PMID: 26561873

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