Synthesis of Axially and Centrally Chiral N‐Alkenyl Indoles by Asymmetric Rh‐Catalyzed [2 + 2 + 2] Cycloaddition
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DOI: 10.1002/cctc.202401143
Abstract: Axially chiral indoline‐based scaffolds are virtually universal in biological and pharmaceutical compounds. In this study, we demonstrate the Rh‐catalyzed asymmetric [2 + 2 + 2] cycloaddition of 1,6‐enynes with steric hindered N‐alkynyl indoles, which enables simultaneous construction of both… read more here.
Keywords: axially centrally; chiral alkenyl; synthesis axially; alkenyl indoles ... See more keywords
Atroposelective Synthesis of Axially Chiral C2-Arylindoles via Rhodium-Catalyzed Asymmetric C-H Bond Insertion.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c01818
Abstract: A highly efficient rhodium-catalyzed formal C-H insertion reaction between indoles and 1-diazonaphthoquinones has been established, providing a novel protocol for the atroposelective synthesis of axially chiral C2-arylindoles (up to 99:1 er) under mild reaction conditions.… read more here.
Keywords: chiral arylindoles; rhodium catalyzed; axially chiral; synthesis axially ... See more keywords
Enantioselective Synthesis of Axially Chiral Figure-Eight Spirocycloparaphenylenes via Rh-Catalyzed Intermolecular [2 + 2 + 2] Cycloaddition.
Sign Up to like & getrecommendations! Published in 2023 at "Organic letters"
DOI: 10.1021/acs.orglett.3c00895
Abstract: We have achieved the enantioselective synthesis of axially chiral figure-eight spiro[9.9]cycloparaphenylene (CPP) tetracarboxylates with up to 75:25 er via the cationic Rh(I)/(R)-H8-BINAP complex-catalyzed chemo-, regio-, and enantioselective intermolecular double [2 + 2 + 2] cycloaddition… read more here.
Keywords: enantioselective synthesis; figure eight; axially chiral; synthesis axially ... See more keywords
Catalytic Atroposelective Synthesis of Axially Chiral Heterobiaryl Oxime Ethers via the One-Step Dynamic Kinetic Condensation Reaction.
Sign Up to like & getrecommendations! Published in 2024 at "Organic letters"
DOI: 10.1021/acs.orglett.4c00479
Abstract: The catalytic atroposelective synthesis of axially chiral heterobiaryls was first developed through the direct one-step dynamic kinetic condensation reaction with the simple transformation of the C═O bond to the C═N bond, delivering a series of… read more here.
Keywords: axially chiral; atroposelective synthesis; one step; synthesis axially ... See more keywords
Enantioselective Synthesis of Axially Chiral 1,8-Diarylnaphthalenes by Rh-Catalyzed [2 + 2 + 2] Cycloaddition and Evaluation of Their Chiroptical Properties.
Sign Up to like & getrecommendations! Published in 2025 at "Organic letters"
DOI: 10.1021/acs.orglett.5c01037
Abstract: Intermolecular [2 + 2 + 2] cycloaddition of 1-alkynyl-8-arylnaphthalenes with 1,6-diynes proceeded in the presence of Rh-chiral BINAP derivative catalysts to give axially chiral 1,8-diarylnaphthalenes in excellent yields along with up to perfect enantioselectivity. As… read more here.
Keywords: enantioselective synthesis; diarylnaphthalenes catalyzed; axially chiral; synthesis axially ... See more keywords
Atroposelective Transfer Hydrogenation of Biaryl Aminals via Dynamic Kinetic Resolution. Synthesis of Axially Chiral Diamines
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DOI: 10.1021/acscatal.1c00571
Abstract: An efficient dynamic kinetic resolution (DKR) approach for the synthesis of axially chiral diamines has been developed on the basis of a ruthenium-catalyzed enantioselective transfer hydrogenation.... read more here.
Keywords: kinetic resolution; dynamic kinetic; transfer hydrogenation; axially chiral ... See more keywords
Rh(I)-Catalyzed Modular Synthesis of Axially Chiral Alkylidene Azacycloalkanes
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DOI: 10.1021/acscentsci.5c00232
Abstract: The structural prevalence of chiral N-bridged cyclic scaffolds in pharmacologically relevant substances originates from their multifaceted biofunctional capacities, particularly in privileged natural product architectures. Despite advances in central chirality, the precise and expeditious construction of… read more here.
Keywords: axially chiral; catalyzed modular; synthesis axially; chiral alkylidene ... See more keywords
Synthesis of Axially Chiral 2,2'-Bisphosphobiarenes via a Nickel-Catalyzed Asymmetric Ullmann Coupling: General Access to Privileged Chiral Ligands without Optical Resolution.
Sign Up to like & getrecommendations! Published in 2021 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.0c12843
Abstract: We report an asymmetric homocoupling of ortho-(iodo)arylphosphine oxides and ortho-(iodo)arylphosphonates resulting in highly enantioenriched axially chiral bisphosphine oxides and bisphosphonates. These products are readily converted to enantioenriched biaryl bisphosphines without need for chiral auxiliaries or… read more here.
Keywords: bisphosphobiarenes via; synthesis axially; optical resolution; chiral bisphosphobiarenes ... See more keywords
Asymmetric Azide-Alkyne Cycloaddition with Ir(I)/Squaramide Cooperative Catalysis: Atroposelective Synthesis of Axially Chiral Aryltriazoles.
Sign Up to like & getrecommendations! Published in 2022 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.2c02563
Abstract: An Ir(I)/squaramide cooperative catalytic strategy for atroposelective synthesis of axially chiral aryltriazoles has been developed for the first time. Diverse structurally novel aryltriazole skeletons that cannot be accessed by traditional click reactions were synthesized in… read more here.
Keywords: chiral aryltriazoles; squaramide cooperative; axially chiral; synthesis axially ... See more keywords
Nickel-Catalyzed Asymmetric Propargylation for the Synthesis of Axially Chiral 1,3-Disubstituted Allenes.
Sign Up to like & getrecommendations! Published in 2022 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.2c10863
Abstract: The general enantioselective catalytic synthesis of axially chiral 1,3-disubstituted allenes from readily available racemic propargylic alcohol derivatives remains a long-standing challenge in organic synthesis. Here we report an efficient nickel-catalyzed asymmetric propargylic substitution reaction/Myers rearrangement… read more here.
Keywords: disubstituted allenes; nickel catalyzed; synthesis; axially chiral ... See more keywords
Enantioselective Synthesis of Axially Chiral Alkylidenecyclobutanes via Palladium-Catalyzed N-Tosylhydrazone-Based Carbene Coupling.
Sign Up to like & getrecommendations! Published in 2025 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.5c04354
Abstract: The synthesis of axially chiral alkylidenecyclobutanes remains challenging due to the requirement of both an efficient asymmetric catalytic system and preservation of its inherent strained ring structure. We herein disclose an enantioselective carbene cross-coupling reaction… read more here.
Keywords: enantioselective synthesis; axially chiral; synthesis axially; carbene ... See more keywords