ArticleJournal of the American Chemical Society2016
Catalytic Enantioselective Dihalogenation and the Selective Synthesis of (-)-Deschloromytilipin A and (-)-Danicalipin A.
Article in Journal of the American Chemical Society, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 31 papers.
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Who cites it
31 citing papers in PubMed.
- Internally Directed Stereochemical Alteration of Alkene Dihalogenation.The Journal of organic chemistry · 2026Article
- Alternating-Polarity Electrolysis Enables Efficient Enantioselective Semipinacol Rearrangement Using Sodium Chloride.Journal of the American Chemical Society · 2026Article
- Enantioselective synthesis of allylic boronates bearing a stereodefined (Organic chemistry frontiers : an international journal of organic chemistry · 2026Article
- Syntheses of Marine Natural Products via Matteson Homologations and Related Processes.Marine drugs · 2025Review
- Stereospecific syn-dichlorination of allylic amines enabled by identification of a superior stereo-directing group.Communications chemistry · 2024Article
- Photocatalytic, modular difunctionalization of alkenes enabled by ligand-to-metal charge transfer and radical ligand transfer.Chemical science · 2023Article
- Naturally Occurring Organohalogen Compounds-A Comprehensive Review.Progress in the chemistry of organic natural products · 2023Review
- Catalytic Chemo-, Regio-, Diastereo-, and Enantioselective Bromochlorination of Unsaturated Systems Enabled by Lewis Base-Controlled Chloride Release.Journal of the American Chemical Society · 2022Article
- Automated iterative CspNature · 2022Article
- The Electrochemical cis-Chlorination of Alkenes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Catalytic enantioselective bromohydroxylation of cinnamyl alcohols.RSC advances · 2021Article
- Ritter-enabled catalytic asymmetric chloroamidation of olefins.Chemical science · 2020Article
- Halogenation-Dependent Effects of the Chlorosulfolipids ofACS chemical biology · 2020Article
- Catalytic Dynamic Kinetic Resolutions in Tandem to Construct Two-Axis Terphenyl Atropisomers.Journal of the American Chemical Society · 2020Article
- An Enamide-Based Domino Reaction for a Highly Stereoselective Synthesis of Tetrahydropyrans.Angewandte Chemie (International ed. in English) · 2019Article
- Organoselenium-catalyzed enantioselectiveTetrahedron · 2019Article
- Enantioselective Synthesis of Azamerone.Journal of the American Chemical Society · 2019Article
- Dative Directing Group Effects in Ti-Catalyzed [2+2+1] Pyrrole Synthesis: Chemo- and Regioselective Alkyne Heterocoupling.ACS catalysis · 2019Article
- Catalytic Regio- and Enantioselective Haloazidation of Allylic Alcohols.Journal of the American Chemical Society · 2018Article
- Catalytic Enantioselective Dihalogenation in Total Synthesis.Accounts of chemical research · 2018Review
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4 authors.
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Abstract
A titanium-based catalytic enantioselective dichlorination of simple allylic alcohols is described. This dichlorination reaction provides stereoselective access to all common dichloroalcohol building blocks used in syntheses of chlorosulfolipid natural products. An enantioselective synthesis of ent-(-)-deschloromytilipin A and a concise, eight-step synthesis of ent-(-)-danicalipin A are executed and employ the dichlorination reaction as the first step. Extension of this system to enantioselective dibromination and its use in the synthesis of pentabromide stereoarrays relevant to bromosulfolipids is reported. The described dichlorination and dibromination reactions are capable of exerting diastereocontrol in complex settings allowing X-ray crystal structure analysis of natural and unnatural diastereomers of polyhalogenated stereohexads.
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