ArticleAngewandte Chemie (International ed. in English)2022
Unusual Enantiodivergence in Chiral Brønsted Acid-Catalyzed Asymmetric Allylation with β-Alkenyl Allylic Boronates.
Article in Angewandte Chemie (International ed. in English), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed.
- Flipping the Card With Enantiodivergent Organocatalysis.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Review
- 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
- Enantioselective Syntheses of Secondary Alkylboronates via Asymmetric Regioselective Reduction of 1,3-Dienylboronates.Angewandte Chemie (International ed. in English) · 2026Article
- Functional Group Transposition Enabled by Palladium and Photo Dual Catalysis.Journal of the American Chemical Society · 2025Article
- Stereo- and Enantioselective Syntheses of (Organic letters · 2025Article
- Highly Stereo- and Enantioselective Syntheses of δ-Alkyl-Substituted (Organic letters · 2025Article
- Stereo- and Enantioselective Syntheses of 1,2-Oxaborinan-3-enes and δ-Boryl-Substituted Homoallylic Alcohols.Organic letters · 2024Article
- Copper-Catalyzed Asymmetric Acylboration of 1,3-Butadienylboronate with Acyl Fluorides.Angewandte Chemie (International ed. in English) · 2023Article
- Dimerization of confined Brønsted acids in enantioselective organocatalytic reactions.Chemical science · 2023Article
- Stereoselective syntheses of 2-methyl-1,3-diol acetalsChemical science · 2023Article
- Electrostatic Interactions in Asymmetric Organocatalysis.Accounts of chemical research · 2023Article
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Authors and funding
7 authors.
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Abstract
We report herein a rare example of enantiodivergent aldehyde addition with β-alkenyl allylic boronates via chiral Brønsted acid catalysis. 2,6-Di-9-anthracenyl-substituted chiral phosphoric acid-catalyzed asymmetric allylation using β-vinyl substituted allylic boronate gave alcohols with R absolute configuration. The sense of asymmetric induction of the catalyst in these reactions is opposite to those in prior reports. Moreover, in the presence of the same acid catalyst, the reactions with β-2-propenyl substituted allylic boronate generated homoallylic alcohol products with S absolute configuration. Unusual substrate-catalyst C-H⋅⋅⋅π interactions in the favoured reaction transition state were identified as the origins of observed enantiodivergence through DFT computational studies.
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