Unknown

Dataset Information

0

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

Json Xml
altmetric image

Publications

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]

Similar Datasets

Unknown Catalytic asymmetric synthesis of quaternary trifluoromethyl α- to ε-amino acid derivatives <i>via</i> umpolung allylation/2-aza-Cope rearrangement.
| S-EPMC8162408 | biostudies-literature
Unknown Catalytic asymmetric reactions for organic synthesis: the combined C-H activation/Cope rearrangement.
| S-EPMC397407 | biostudies-literature
Unknown Enantioconvergent Cross-Couplings of Alkyl Electrophiles: The Catalytic Asymmetric Synthesis of Organosilanes.
| S-EPMC6399024 | biostudies-literature
Unknown Total synthesis of sedum alkaloids via catalyst controlled aza-Cope rearrangement and hydroformylation with formaldehyde.
| S-EPMC3582941 | biostudies-literature
Unknown Aza-cope rearrangement-mannich cyclizations for the formation of complex tricyclic amines: stereocontrolled total synthesis of (+/-)-gelsemine.
| S-EPMC2570375 | biostudies-literature
Unknown Catalytic, asymmetric indolizidinone aza-quaternary stereocenter synthesis: expedient synthesis of the cylindricine alkaloid core.
| S-EPMC3809156 | biostudies-literature
Unknown Catalytic Asymmetric Staudinger-aza-Wittig Reaction for the Synthesis of Heterocyclic Amines.
| S-EPMC7371345 | biostudies-literature
Unknown Formal enantioconvergent substitution of alkyl halides via catalytic asymmetric photoredox radical coupling.
| S-EPMC6015005 | biostudies-literature
Unknown Expedient synthesis of fused azepine derivatives using a sequential rhodium(II)-catalyzed cyclopropanation/1-aza-Cope rearrangement of dienyltriazoles.
| S-EPMC4266427 | biostudies-literature
Unknown Synergistic catalysis for cascade allylation and 2-aza-cope rearrangement of azomethine ylides.
| S-EPMC6453969 | biostudies-literature