ArticleNature chemistry2013
Enantioselective silyl protection of alcohols promoted by a combination of chiral and achiral Lewis basic catalysts.
Article in Nature chemistry, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed.
- Article
- Organocatalytic Asymmetric Synthesis of Si-Stereogenic Siloxanols.ACS catalysis · 2024Article
- Cu-catalysed enantioselective radical heteroatomic S-O cross-coupling.Nature chemistry · 2023Article
- Copper-Catalyzed Asymmetric Sulfonylative Desymmetrization of Glycerol.Molecules (Basel, Switzerland) · 2022Article
- Collective total synthesis of C4-oxygenated securinine-type alkaloids via stereocontrolled diversifications on the piperidine core.Nature communications · 2022Article
- Biomimetic Non-Heme Iron-Catalyzed Epoxidation of Challenging Terminal Alkenes Using Aqueous HMolecules (Basel, Switzerland) · 2019Article
- Delayed catalyst function enables direct enantioselective conversion of nitriles to NHScience (New York, N.Y.) · 2019Article
- C-H Functionalization of Amines via Alkene-Derived Nucleophiles through Cooperative Action of Chiral and Achiral Lewis Acid Catalysts: Applications in Enantioselective Synthesis.Journal of the American Chemical Society · 2018Article
- Alkylative kinetic resolution of vicinal diols under phase-transfer conditions: a chiral ammonium borinate catalysis.Chemical science · 2018Article
- Broad-spectrum kinetic resolution of alcohols enabled by Cu-H-catalysed dehydrogenative coupling with hydrosilanes.Nature communications · 2017Article
- Enantioselective acyl transfer catalysis by a combination of common catalytic motifs and electrostatic interactions.Nature communications · 2016Article
- Mechanism of NHC-Catalyzed Conjugate Additions of Diboron and Borosilane Reagents to α,β-Unsaturated Carbonyl Compounds.Journal of the American Chemical Society · 2015Article
- Parts-per-million level loading organocatalysed enantioselective silylation of alcohols.Nature communications · 2015Article
- Synthesis of 5'-O-DMT-2'-O-TBS Mononucleosides Using an Organic Catalyst.Current protocols in nucleic acid chemistry · 2014Review
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Authors and funding
5 authors.
Funding
Abstract
Catalytic enantioselective monosilylations of diols and polyols furnish valuable alcohol-containing molecules in high enantiomeric purity. These transformations, however, require high catalyst loadings (20-30 mol%) and long reaction times (2-5 days). Here, we report that a counterintuitive strategy involving the use of an achiral co-catalyst structurally similar to the chiral catalyst provides an effective solution to this problem. A combination of seemingly competitive Lewis basic molecules can function in concert such that one serves as an achiral nucleophilic promoter and the other performs as a chiral Brønsted base. On the addition of 7.5-20 mol% of a commercially available N-heterocycle (5-ethylthiotetrazole), reactions typically proceed within one hour, and deliver the desired products in high yields and enantiomeric ratios. In some instances, there is no reaction in the absence of the achiral base, yet the presence of the achiral co-catalyst gives rise to facile formation of products in high enantiomeric purity.
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