ArticleJournal of the American Chemical Society2010
Iridium-catalyzed kinetic asymmetric transformations of racemic allylic benzoates.
Article in Journal of the American Chemical Society, 2010. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed.
- Stereodivergent synthesis of α-fluoro α-azaaryl γ-butyrolactonesFundamental research · 2024Article
- Enantioselective Allylation of Alkenyl Boronates Promotes a 1,2-Metalate Rearrangement with 1,3-Diastereocontrol.Journal of the American Chemical Society · 2021Article
- Enantioselective Synthesis of Alkyl Allyl Ethers via Palladium-Catalyzed Redox-Relay Heck Alkenylation ofIsrael journal of chemistry · 2020Article
- Formation of Chiral Allylic Ethers via an Enantioselective Palladium-Catalyzed Alkenylation of Acyclic Enol Ethers.Journal of the American Chemical Society · 2018Article
- Copper-catalyzed oxidative dehydrogenative carboxylation of unactivated alkanes to allylic esters via alkenes.Journal of the American Chemical Society · 2014Article
- Diastereo- and enantioselective iridium-catalyzed allylation of cyclic ketone enolates: synergetic effect of ligands and barium enolates.Journal of the American Chemical Society · 2014Article
- The regio- and stereospecific intermolecular dehydrative alkoxylation of allylic alcohols catalyzed by a gold(I) N-heterocyclic carbene complex.Chemistry (Weinheim an der Bergstrasse, Germany) · 2013Article
- Origins of enantioselectivity during allylic substitution reactions catalyzed by metallacyclic iridium complexes.Journal of the American Chemical Society · 2012Article
- Enantioselective construction of all-carbon quaternary centers by branch-selective Pd-catalyzed allyl-allyl cross-coupling.Journal of the American Chemical Society · 2011Article
- Catalytic asymmetric synthesis of chiral allylic esters.Journal of the American Chemical Society · 2005Article
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4 authors.
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Abstract
Versatile methods for iridium-catalyzed, kinetic asymmetric substitution of racemic, branched allylic esters are reported. These reactions occur with a variety of aliphatic, aryl, and heteroaryl allylic benzoates to form the corresponding allylic substitution products in high yields (74-96%) with good to excellent enantioselectivity (84-98% ee) with a scope that encompasses a range of anionic carbon and heteroatom nucleophiles. These kinetic asymmetric processes occur with distinct stereochemical courses for racemic aliphatic and aromatic allylic benzoates, and the high reactivity of branched allylic benzoates enables enantioselective allylic substitutions that are slow or poorly selective with linear allylic electrophiles.
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