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Rhodium-catalyzed sequential allylic amination and olefin hydroacylation reactions: enantioselective synthesis of seven-membered nitrogen heterocycles.
Angew Chem Int Ed Engl. 2014 Apr 01; 53(14):3688-92.AC

Abstract

Dynamic kinetic asymmetric amination of branched allylic acetimidates has been applied to the synthesis of 2-alkyl-dihydrobenzoazepin-5-ones. These seven-membered-ring aza ketones are prepared in good yield with high enantiomeric excess by rhodium-catalyzed allylic substitution with 2-amino aryl aldehydes followed by intramolecular olefin hydroacylation of the resulting alkenals. This two-step procedure is amenable to varied functionality and proves useful for the enantioselective preparation of these ring systems.

Authors+Show Affiliations

Department of Chemistry, The University of Iowa, Iowa City, IA 52242 (USA) http://chem.uiowa.edu/nguyen-research-group.No affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

24591294

Citation

Arnold, Jeffrey S., et al. "Rhodium-catalyzed Sequential Allylic Amination and Olefin Hydroacylation Reactions: Enantioselective Synthesis of Seven-membered Nitrogen Heterocycles." Angewandte Chemie (International Ed. in English), vol. 53, no. 14, 2014, pp. 3688-92.
Arnold JS, Mwenda ET, Nguyen HM. Rhodium-catalyzed sequential allylic amination and olefin hydroacylation reactions: enantioselective synthesis of seven-membered nitrogen heterocycles. Angew Chem Int Ed Engl. 2014;53(14):3688-92.
Arnold, J. S., Mwenda, E. T., & Nguyen, H. M. (2014). Rhodium-catalyzed sequential allylic amination and olefin hydroacylation reactions: enantioselective synthesis of seven-membered nitrogen heterocycles. Angewandte Chemie (International Ed. in English), 53(14), 3688-92. https://doi.org/10.1002/anie.201310354
Arnold JS, Mwenda ET, Nguyen HM. Rhodium-catalyzed Sequential Allylic Amination and Olefin Hydroacylation Reactions: Enantioselective Synthesis of Seven-membered Nitrogen Heterocycles. Angew Chem Int Ed Engl. 2014 Apr 1;53(14):3688-92. PubMed PMID: 24591294.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Rhodium-catalyzed sequential allylic amination and olefin hydroacylation reactions: enantioselective synthesis of seven-membered nitrogen heterocycles. AU - Arnold,Jeffrey S, AU - Mwenda,Edward T, AU - Nguyen,Hien M, Y1 - 2014/03/03/ PY - 2013/11/28/received PY - 2014/02/02/revised PY - 2014/3/5/entrez PY - 2014/3/5/pubmed PY - 2014/11/11/medline KW - allylic amination KW - asymmetric catalysis KW - intramolecular hydroacylation KW - nitrogen heterocycles KW - rhodium SP - 3688 EP - 92 JF - Angewandte Chemie (International ed. in English) JO - Angew Chem Int Ed Engl VL - 53 IS - 14 N2 - Dynamic kinetic asymmetric amination of branched allylic acetimidates has been applied to the synthesis of 2-alkyl-dihydrobenzoazepin-5-ones. These seven-membered-ring aza ketones are prepared in good yield with high enantiomeric excess by rhodium-catalyzed allylic substitution with 2-amino aryl aldehydes followed by intramolecular olefin hydroacylation of the resulting alkenals. This two-step procedure is amenable to varied functionality and proves useful for the enantioselective preparation of these ring systems. SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/24591294/Rhodium_catalyzed_sequential_allylic_amination_and_olefin_hydroacylation_reactions:_enantioselective_synthesis_of_seven_membered_nitrogen_heterocycles_ L2 - https://doi.org/10.1002/anie.201310354 DB - PRIME DP - Unbound Medicine ER -