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Record W4411907594 · doi:10.1002/adsc.70013

Three‐Component Synthesis of <i>γ</i>‐Amino Esters with <i>α</i>‐Quaternary Carbon Centers via NHC/Photoredox Dual Catalysis

2025· article· en· W4411907594 on OpenAlex
Adam X. Wayment, Karl A. Scheidt

Why this work is in the frame

A frame that forgets how it found something cannot be audited. These are the routes that admitted this work.

fundA Canadian funder is recorded on the work.
no affNo Canadian affiliation: this work is invisible to an affiliation-only frame.
No Canadian affiliation. An affiliation-only frame, the usual design, would never have seen this work. It is one of the works that make the case for inverting the frame.

Bibliographic record

VenueAdvanced Synthesis & Catalysis · 2025
Typearticle
Languageen
FieldChemistry
TopicRadical Photochemical Reactions
Canadian institutionsnot available
FundersNational Institute of General Medical SciencesMcGill UniversityNorthwestern University
KeywordsChemistryQuaternary carbonAmino acidCatalysisCombinatorial chemistryPhotoredox catalysisDual roleOrganic chemistryMicellePhotocatalysisEnantioselective synthesisAqueous solutionBiochemistry

Abstract

fetched live from OpenAlex

γ ‐Amino acid derivatives are important motifs in medicinal chemistry and have shown wide applicability as inhibitory neurotransmitters. An important class of these compounds feature α , α ‐disubstitution. However, established routes for the direct synthesis of γ ‐amino esters bearing α ‐quaternary centers are severely limited in both number of available routes and scope of the transformation. Herein a method is presented for the three‐component synthesis of α , α ‐disubstituted γ ‐amino esters via N‐heterocyclic carbene/photoredox dual catalysis. This reaction involves in situ formation of an acyl azolium ester which undergoes photocatalytic reduction to the key stabilized alkoxycarbonyl radical. This methodology is shown to be capable of synthesizing a wide variety of γ ‐amino esters with various α ‐quaternary centers in moderate to good yields, including a derivative of the drug loperamide. The diversity of products that can be synthesized facilitates the rapid generation of libraries of γ ‐amino acid derived compounds.

Fetched live from OpenAlex and de-inverted. Abstracts are not stored in this database: the inverted indexes are 8.6 GB of the frame’s 9.3 GB of text, and the host has 13 GB free.

Full frame distilled prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. Learned from the 10,348 direct Codex labels and 10,348 direct Gemma labels. Candidate is the union of thresholded teacher heads; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels or direct frontier model labels.

metaresearch head score (Codex)0.000
metaresearch head score (Gemma)0.001
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesMeta-epidemiology (narrow)
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Bench or experimental · Consensus signal: Bench or experimental
GenreCandidate signal: Empirical · Consensus signal: Empirical
Teacher disagreement score0.030
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.001
Meta-epidemiology (narrow)0.0010.001
Meta-epidemiology (broad)0.0010.001
Bibliometrics0.0000.001
Science and technology studies0.0000.001
Scholarly communication0.0000.000
Open science0.0010.000
Research integrity0.0000.000
Insufficient payload (model declined to judge)0.0000.000

Machine scores (provisional)

The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.

Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.

Opus teacher head0.005
GPT teacher head0.217
Teacher spread0.212 · how far apart the two teachers sit on this one work
Validation statusscore_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it