ArticleAngewandte Chemie (International ed. in English)2016
Regio- and Stereoselective Homologation of 1,2-Bis(Boronic Esters): Stereocontrolled Synthesis of 1,3-Diols and Sch 725674.
Article in Angewandte Chemie (International ed. in English), 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 22 papers.
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Who cites it
22 citing papers in PubMed.
- Enantioenriched Alkylboron Synthesis Via a Chiral Diborylalkane Platform.Journal of the American Chemical Society · 2026Article
- Converting 1,1-Bisborylalkanes into 1,2-Bisborylalkanes Enabled by Iron Ligand-to-Metal Charge Transfer (LMCT) Photocatalysis.Angewandte Chemie (International ed. in English) · 2026Article
- Site-Selective Activation and Stereospecific Functionalization of Bis(boronic Esters) Derived from 2-Alkenes: Construction of Propionates and Other 1,2-Difunctional Motifs.Angewandte Chemie (International ed. in English) · 2024Article
- Enantio- and Regioselective Cascade Hydroboration of Methylenecyclopropanes for Facile Access to Chiral 1,3- and 1,4-Bis(boronates).Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Platinum-Catalyzed Enantioselective Diboration of Monosubstituted Alkenes.Organic syntheses; an annual publication of satisfactory methods for the preparation of organic chemicals · 2024Article
- 1,2-Metallate Rearrangement as a Toolbox for the Synthesis of Allylic Alcohols.The Journal of organic chemistry · 2023Article
- Enantioselective Suzuki cross-coupling of 1,2-diboryl cyclopropanes.Chemical science · 2023Article
- Copper-Catalyzed Coupling of Alkyl Vicinal Bis(boronic Esters) to an Array of Electrophiles.Journal of the American Chemical Society · 2022Article
- Dual Nickel/Photoredox-Catalyzed Site-Selective Cross-Coupling of 1,2-Bis-Boronic Esters Enabled by 1,2-Boron Shifts.Angewandte Chemie (International ed. in English) · 2022Article
- Stereocontrolled Total Synthesis of Bastimolide B Using Iterative Homologation of Boronic Esters.Journal of the American Chemical Society · 2022Article
- Selective, Transition Metal-free 1,2-Diboration of Alkyl Halides, Tosylates, and Alcohols.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Selective Coupling of 1,2-Bis-Boronic Esters at the more Substituted Site through Visible-Light Activation of Electron Donor-Acceptor Complexes.Angewandte Chemie (International ed. in English) · 2022Article
- Synthesis of 1,3-Bis-(boryl)alkanes through Boronic Ester Induced Consecutive Double 1,2-Migration.Angewandte Chemie (International ed. in English) · 2020Article
- Zirconium-Catalyzed Atom-Economical Synthesis of 1,1-Diborylalkanes from Terminal and Internal Alkenes.Angewandte Chemie (International ed. in English) · 2020Article
- 1,2-Boron Shifts of β-Boryl Radicals Generated from Bis-boronic Esters Using Photoredox Catalysis.Journal of the American Chemical Society · 2019Article
- Site-Selective Mono-Oxidation of 1,2-Bis(boronates).Organic letters · 2019Article
- Cascade Reaction by Chemo- and Biocatalytic Approaches to Obtain Chiral Hydroxy Ketones andChemistryOpen · 2018Article
- Carbohydrate/DBU Cocatalyzed Alkene Diboration: Mechanistic Insight Provides Enhanced Catalytic Efficiency and Substrate Scope.Journal of the American Chemical Society · 2018Article
- Article
- Enantioselective γ-borylation of unsaturated amides and stereoretentive Suzuki-Miyaura cross-coupling.Chemical science · 2017Article
Corrections and comments
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Authors and funding
6 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
1,2-Bis(boronic esters), derived from the enantioselective diboration of terminal alkenes, can be selectively homologated at the primary boronic ester by using enantioenriched primary/secondary lithiated carbamates or benzoates to give 1,3-bis(boronic esters), which can be subsequently oxidized to the corresponding secondary-secondary and secondary-tertiary 1,3-diols with full stereocontrol. The transformation was applied to a concise total synthesis of the 14-membered macrolactone, Sch 725674. The nine-step synthetic route also features a novel desymmetrizing enantioselective diboration of a divinyl carbinol derivative and high-yielding late-stage cross-metathesis and Yamaguchi macrolactonization reactions.
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