ArticleJournal of the American Chemical Society2011
Pinene-derived iminodiacetic acid (PIDA): a powerful ligand for stereoselective synthesis and iterative cross-coupling of C(sp3) boronate building blocks.
Article in Journal of the American Chemical Society, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 37 papers.
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Who cites it
37 citing papers in PubMed, 170 citations in OpenAlex.
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- Harnessing the β-boron effect for regioselective Ru-catalyzed hydrosilylation of internal alkynes.Nature communications · 2025Article
- NHC-Au-Catalyzed Isomerization of Propargylic B(MIDA)s to Allenes and Double Isomerization of Alkynes to 1,3-Dienes.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Reactivity of 1,3-enyne MIDA boronates: exploration of novel 1,2-alkyne shiftChemical science · 2024Article
- Regioselective Electrophilic Addition to Propargylic B(MIDA)s Enabled by β-Boron Effect.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2023Article
- Regiocontrolled allylic functionalization of internal alkeneChemical science · 2022Article
- The pinene scaffold: its occurrence, chemistry, synthetic utility, and pharmacological importance.RSC advances · 2022Review
- Hypervalent iodine-mediated β-difluoroalkylboron synthesisChemical science · 2022Article
- Electrophilic Fluorination of Alkenes via Bora-Wagner-Meerwein Rearrangement. Access to β-Difluoroalkyl Boronates.Angewandte Chemie (International ed. in English) · 2021Article
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- Mechanism and Scope of Nickel-Catalyzed Decarbonylative Borylation of Carboxylic Acid Fluorides.Journal of the American Chemical Society · 2019Article
- Regioselective radical α-borylation of α,β-unsaturated carbonyl compounds for direct synthesis of α-borylcarbonyl molecules.Nature communications · 2019Article
- Axial shielding of Pd(II) complexes enables perfect stereoretention in Suzuki-Miyaura cross-coupling of CspNature communications · 2019Article
- Reductive α-borylation of α,β-unsaturated esters using NHC-BHChemical science · 2019Article
- The Molecular Industrial Revolution: Automated Synthesis of Small Molecules.Angewandte Chemie (International ed. in English) · 2018Review
- Toward Generalization of Iterative Small Molecule Synthesis.Nature reviews. Chemistry · 2018Article
- Multicomponent mapping of boron chemotypes furnishes selective enzyme inhibitors.Nature communications · 2017Article
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Abstract
Efficient access to chiral C(sp(3)) boronates in stereochemically pure form is critical for realizing the substantial potential of such building blocks in complex-molecule synthesis. We herein report that a pinene-derived iminodiacetic acid (PIDA) ligand enables the highly diastereoselective synthesis of a wide range of oxiranyl C(sp(3)) boronates from the corresponding olefins. These oxiranyl PIDA boronates, in turn, can be readily transformed into unprecedented stable α-boryl aldehydes via a novel 1,2-migration of the boronate group that proceeds with complete maintenance of stereochemical purity. B-Protected haloboronic acids containing dual sp(3)-hybridized C centers are readily accessible via this platform, and the herein demonstrated capacity for stereocontrolled iterative C(sp(3)) cross-coupling with this novel type of bifunctional reagent to access a medicinally important chiral small-molecule target in highly enantioenriched form represents a substantial advance for the building-block-based approach to synthesis.
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