Recent Advances in the Stereoselective Additions of Allylic Boronates to Carbonyl Compounds
Bibliographic record
Abstract
Abstract The addition of allylboronates to carbonyl compounds remains an invaluable transformation in synthetic organic chemistry for the stereoselective synthesis of a wide variety of substituted homoallylic alcohols. The use of allylboronates is an exceptionally attractive tool, in part due to the stability of organoboron nucleophiles and the inherently high and predictable stereoselectivity consistently observed. Herein, key advances regarding the thermal and catalyzed allylboration of aldehydes and ketones from the past decade are summarized, with a focus on aspects concerning the scope, mechanism, and stereoselectivity. Notably, novel modes of activation are described for both enantioenriched α‐substituted allylboronates and catalytic enantioselective additions of achiral boronates using chiral protic acids and organocatalysts. A number of innovative metal‐catalyzed enantioselective borylation approaches to allylboronates and their subsequent use as substrates, including bimetallic double allylation reagents, are also highlighted. The current innovative progress and limitations in the field of carbonyl allylboration are discussed.
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How this classification was reachedexpand
Full frame machine prediction
Teacher imitationNot calibrated prevalence, not ground truth. Human validation pending. The Gemma side is a direct model label for every work in the frame, read from the title-only record. The Codex side is a classifier learned from the 10,348 direct Codex labels and calibrated to design-weighted sample rates; fields without enough sample support carry no Codex call. Candidate is the union of the two sides; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels.
Distilled classifier scores by category (both heads)
| Category | Codex | Gemma |
|---|---|---|
| Metaresearch | 0.001 | 0.000 |
| Meta-epidemiology (narrow) | 0.001 | 0.000 |
| Meta-epidemiology (broad) | 0.000 | 0.000 |
| Bibliometrics | 0.001 | 0.001 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.001 |
| Open science | 0.000 | 0.001 |
| Research integrity | 0.000 | 0.000 |
| Insufficient payload (model declined to judge) | 0.003 | 0.002 |
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.
score_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from itClassification
machine, unvalidatedMachine predicted; a candidate call from one source (direct Gemma or distilled Codex), not a consensus.
How this classification was reached, model by model and score by score, is at the end of the page under "How this classification was reached".