ArticleAngewandte Chemie (International ed. in English)2019
Catalytic Enantioselective Synthesis of 1,4-Keto-Alkenylboronate Esters and 1,4-Dicarbonyls.
Article in Angewandte Chemie (International ed. in English), 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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8 citing papers in PubMed.
- (Poly)Borylated Species as Modern Reactive Groups toward Unusual Synthetic Applications.Angewandte Chemie (International ed. in English) · 2026Review
- Palladium-Catalyzed Atroposelective Suzuki-Miyaura Coupling to Construct Axially Chiral Tetra-Substituted α-Boryl Styrenes.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Stereoselective Control of the Cu Activation of β,β-Diboryl Acrylates for Allylic Coupling Protocols with Concomitant Lactonization.Organic letters · 2024Article
- Site-Selective (Z)-α-Borylalkenyl Copper Systems for Nucleophilic Stereodefined Allylic Coupling.Angewandte Chemie (International ed. in English) · 2022Article
- Boron-Promoted Deprotonative Conjugate Addition: Geminal Diborons as Soft Pronucleophiles and Acyl Anion Equivalents.The Journal of organic chemistry · 2022Article
- Solvent-free hydroboration of alkynes catalyzed by an NHC-cobalt complex.RSC advances · 2022Article
- Carbene-catalyzed enantioselective annulation of dinucleophilic hydrazones and bromoenals for access to aryl-dihydropyridazinones and related drugs.Chemical science · 2021Article
- Stereoselective Diels-Alder Reactions ofJournal of the American Chemical Society · 2021Article
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Abstract
A catalytic enantioselective method for the synthesis of 1,4-keto-alkenylboronate esters by a rhodium-catalyzed conjugate addition pathway is disclosed. A variety of novel, bench-stable alkenyl gem-diboronate esters are synthesized. These easily accessible reagents react smoothly with a collection of cyclic α,β-unsaturated ketones, generating a new C-C bond and stereocenter. Products are isolated in up to 99 % yield with greater than 20:1 E/Z and greater than 99:1 e.r. Mechanistic studies show the site-selectivity of transmetalation and reactivity is ligand dependent. The utility of the approach is highlighted by gram-scale synthesis of enantioenriched cyclic 1,4-diketones, and stereoselective transformations of the products by hydrogenation, allylation, and isomerization.
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