MétaCan
Menu
Back to cohort
Record W2949263468 · doi:10.1002/0471264180.or073.01

Allylboration of Carbonyl Compounds

2009· book· en· W2949263468 on OpenAlex

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.

affAt least one author lists a Canadian institution in the pinned OpenAlex snapshot.

Bibliographic record

VenueOrganic reactions · 2009
Typebook
Languageen
FieldChemistry
TopicChemical Synthesis and Reactions
Canadian institutionsUniversity of Alberta
Fundersnot available
KeywordsReagentChemistryAllylic rearrangementStereoselectivityOrganic chemistryAlkeneEnantioselective synthesisNucleophileContext (archaeology)Combinatorial chemistryOrganic synthesisCatalysis

Abstract

fetched live from OpenAlex

Abstract Allylic boron compounds have gained a prominent status in organic synthesis for their ability to add with high stereoselectivity to carbonyl compounds such as aldehydes, making them a methodology of choice for the preparation of acetate and propionate units found in several classes of natural products. This remarkable reaction process was discovered in 1964, only to become popular in the 1980s. Using either the dialkylborane or boronate reagents, both the thermal uncatalyzed reaction and the more recent acid‐catalyzed procedures can provide homoallylic alcohol products in high enantioselectivity. The wide of range of possibilities for substitution on the reagent's allylic unit has led to the development of numerous reagents, and the residual alkene unit in the products confers to allylboration chemistry a unique versatility. This chapter presents an exhaustive survey of the useful reagents and their associated carbonyl substrates employed in organic synthesis. The mechanisms and parameters of the reaction are discussed, along with an overview of the different preparative methods for allylic boron reagents. The scope and limitations of these reagents in enantioselective additions, doubly diastereoselective additions, tandem reactions, and other variants is emphasized in the context of applications in natural product synthesis. The literature is covered through early 2006.

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)0.000
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesMeta-epidemiology (narrow), Insufficient payload (model declined to judge)
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Bench or experimental · Consensus signal: none
GenreCandidate signal: Other · Consensus signal: Other
Teacher disagreement score0.777
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.000
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0000.000
Research integrity0.0010.001
Insufficient payload (model declined to judge)0.0050.000

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 head0.010
GPT teacher head0.216
Teacher spread0.206 · 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