ArticleThe Journal of organic chemistry2021
Tethered Silanoxyiodination of Alkenes.
Article in The Journal of organic chemistry, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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Who cites it
13 citing papers in PubMed.
- Large-Scale Syntheses of Silanoxy-TetrahydrofuransOrganic syntheses; an annual publication of satisfactory methods for the preparation of organic chemicals · 2025Article
- Taming Tethered Nitreniums for Alkene Functionalization Reactions.The Journal of organic chemistry · 2024Article
- Intramolecular Silanoxy-Michael Reactions with Pendant Nitroalkenes: Racemic and Enantioselective.The Journal of organic chemistry · 2024Article
- Fun With Unusual Functional Groups: Sulfamates, Phosphoramidates, and Di-tert-butyl Silanols.European journal of organic chemistry · 2024Article
- Ring Opening of Aziridines by Pendant Silanols Allows for Stereospecific Preparations of 1'-Amino-tetrahydrofurans.The Journal of organic chemistry · 2023Article
- Dancing Silanols: Stereospecific Rearrangements of Silanol Epoxides into Silanoxy-Tetrahydrofurans and Silanoxy-Tetrahydropyrans.Organic chemistry frontiers : an international journal of organic chemistry · 2023Article
- Covalent Tethers for Precise Amino Alcohol Syntheses: Ring Opening of Epoxides by Pendant Sulfamates and Sulfamides.Organic letters · 2023Article
- Large Scale Epoxide Opening by a Pendant Silanol.Organic syntheses; an annual publication of satisfactory methods for the preparation of organic chemicals · 2023Article
- Ring Opening of Aziridines by Pendant Silanols Allows for Preparations of (±)-Clavaminol H, (±)-Des-Acetyl-Clavaminol H, (±)-Dihydrosphingosine, and (±)-Organic letters · 2022Article
- Highly Stereospecific Cyclizations of Homoallylic Silanols.The Journal of organic chemistry · 2022Article
- Hydroxyselenylation and Tethered Silanoxyselenylation of Allylic Silanols.The Journal of organic chemistry · 2022Article
- Ring Opening of Epoxides by Pendant Silanols.Organic letters · 2022Article
- Unusual Rearrangement-Remercuration Reactions of Allylic Silanols.Organic chemistry frontiers : an international journal of organic chemistry · 2021Article
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Authors and funding
5 authors.
Funding
Abstract
We present the first examples of tethered silanoxyiodination reactions of allylic alcohols. The products are useful silanediol organoiodide synthons and are formed with high regioselectivity and diastereocontrol. The reaction is scalable greater than 10-fold without loss of yield or selectivity. Furthermore, the products are starting materials for further transformations, including deiodination, C-N bond installation, epoxide synthesis, and desilylation. DFT calculations provide a basis for understanding the exquisite 6-
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