Unknown

Dataset Information

0

Enantioconvergent synthesis of functionalized ?-butyrolactones via (3 + 2)-annulation.

ABSTRACT: A dynamic kinetic resolution of ?-halo ?-keto esters in an asymmetric homoenolate reaction is described. A chiral N-hetereocyclic carbene catalyzes the a(3) ? d(3)-umpolung addition of ?,?-enals to racemic ?-keto esters, forming ?-butyrolactones with three contiguous stereocenters. The addition occurs with high regio-, diastereo-, and enantiocontrol. This methodology constitutes an intermolecular DKR process to set three stereocenters during the key bond forming event.

SUBMITTER: Goodman CG 

PROVIDER: S-EPMC4304455 | biostudies-literature | 2015 Jan

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

Enantioconvergent synthesis of functionalized γ-butyrolactones via (3 + 2)-annulation.

Goodman C Guy CG   Walker Morgan M MM   Johnson Jeffrey S JS  

Journal of the American Chemical Society 20141223 1

A dynamic kinetic resolution of β-halo α-keto esters in an asymmetric homoenolate reaction is described. A chiral N-hetereocyclic carbene catalyzes the a(3) → d(3)-umpolung addition of α,β-enals to racemic α-keto esters, forming γ-butyrolactones with three contiguous stereocenters. The addition occurs with high regio-, diastereo-, and enantiocontrol. This methodology constitutes an intermolecular DKR process to set three stereocenters during the key bond forming event. ...[more]

Similar Datasets

Unknown Enantioconvergent synthesis of (+)-aphanorphine via asymmetric Pd-catalyzed alkene carboamination.
| S-EPMC3107030 | biostudies-literature
Unknown Chemoselective Lewis pair polymerization of renewable multivinyl-functionalized ?-butyrolactones.
| S-EPMC5540837 | biostudies-literature
Unknown Synthesis of Polycyclic Imidazolidinones via Amine Redox-Annulation.
| S-EPMC5715285 | biostudies-literature
Unknown Synthesis of functionalized organotrifluoroborates via halomethyltrifluoroborates.
| S-EPMC2528247 | biostudies-literature
Unknown Rapid synthesis of polyprenylated acylphloroglucinol analogs via dearomative conjunctive allylic annulation.
| S-EPMC4140454 | biostudies-literature
Unknown Synthesis of aromatic aza-metallapentalenes from metallabenzene via sequential ring contraction/annulation.
| S-EPMC4391318 | biostudies-other
Unknown Catalytic Asymmetric Synthesis of Butenolides and Butyrolactones.
| S-EPMC5553117 | biostudies-other
Unknown Synthesis of 1,4,6-Tricarbonyl Compounds via Regioselective Gold(I)-Catalyzed Alkyne Hydration and Their Application in the Synthesis of ?-Arylidene-butyrolactones.
| S-EPMC7161055 | biostudies-literature
Unknown Enantioselective synthesis of planar chiral ferrocenes via palladium-catalyzed annulation with diarylethynes.
| S-EPMC3778326 | biostudies-literature
Unknown One-pot synthesis of dicyclopenta-fused peropyrene via a fourfold alkyne annulation.
| S-EPMC7188986 | biostudies-literature