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Regio- and Enantioselective Rhodium-Catalyzed Addition of 1,3-Diketones to Allenes: Construction of Asymmetric Tertiary and Quaternary All Carbon Centers.
Angew Chem Int Ed Engl. 2017 02 06; 56(7):1903-1907.AC

Abstract

An unprecedented highly regio- and enantioselective rhodium-catalyzed addition of 1,3-diketones to terminal and 1,1-disubstituted allenes furnishing asymmetric tertiary and quaternary all-carbon centers is reported. By applying a RhI /phosphoramidite/TFA catalytic system under mild conditions, the desired chiral branched α-allylated 1,3-diketones could be obtained in good to excellent yields, with perfect regioselectivity and in high enantioselectivity. The reaction shows a broad functional-group tolerance on both reaction partners highlighting its synthetic potential.

Authors+Show Affiliations

Institut für Organische Chemie, Albert-Ludwigs-Universität Freiburg, Albertstraβe 21, 79104, Freiburg, Germany.Institut für Organische Chemie, Albert-Ludwigs-Universität Freiburg, Albertstraβe 21, 79104, Freiburg, Germany.

Pub Type(s)

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

Language

eng

PubMed ID

28075513

Citation

Beck, Thorsten M., and Bernhard Breit. "Regio- and Enantioselective Rhodium-Catalyzed Addition of 1,3-Diketones to Allenes: Construction of Asymmetric Tertiary and Quaternary All Carbon Centers." Angewandte Chemie (International Ed. in English), vol. 56, no. 7, 2017, pp. 1903-1907.
Beck TM, Breit B. Regio- and Enantioselective Rhodium-Catalyzed Addition of 1,3-Diketones to Allenes: Construction of Asymmetric Tertiary and Quaternary All Carbon Centers. Angew Chem Int Ed Engl. 2017;56(7):1903-1907.
Beck, T. M., & Breit, B. (2017). Regio- and Enantioselective Rhodium-Catalyzed Addition of 1,3-Diketones to Allenes: Construction of Asymmetric Tertiary and Quaternary All Carbon Centers. Angewandte Chemie (International Ed. in English), 56(7), 1903-1907. https://doi.org/10.1002/anie.201610577
Beck TM, Breit B. Regio- and Enantioselective Rhodium-Catalyzed Addition of 1,3-Diketones to Allenes: Construction of Asymmetric Tertiary and Quaternary All Carbon Centers. Angew Chem Int Ed Engl. 2017 02 6;56(7):1903-1907. PubMed PMID: 28075513.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Regio- and Enantioselective Rhodium-Catalyzed Addition of 1,3-Diketones to Allenes: Construction of Asymmetric Tertiary and Quaternary All Carbon Centers. AU - Beck,Thorsten M, AU - Breit,Bernhard, Y1 - 2017/01/11/ PY - 2016/10/28/received PY - 2017/1/12/pubmed PY - 2017/1/12/medline PY - 2017/1/12/entrez KW - 1,3-diketones KW - allenes KW - asymmetric catalysis KW - rhodium KW - γ,δ-unsaturated ketones SP - 1903 EP - 1907 JF - Angewandte Chemie (International ed. in English) JO - Angew Chem Int Ed Engl VL - 56 IS - 7 N2 - An unprecedented highly regio- and enantioselective rhodium-catalyzed addition of 1,3-diketones to terminal and 1,1-disubstituted allenes furnishing asymmetric tertiary and quaternary all-carbon centers is reported. By applying a RhI /phosphoramidite/TFA catalytic system under mild conditions, the desired chiral branched α-allylated 1,3-diketones could be obtained in good to excellent yields, with perfect regioselectivity and in high enantioselectivity. The reaction shows a broad functional-group tolerance on both reaction partners highlighting its synthetic potential. SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/28075513/Regio__and_Enantioselective_Rhodium_Catalyzed_Addition_of_13_Diketones_to_Allenes:_Construction_of_Asymmetric_Tertiary_and_Quaternary_All_Carbon_Centers_ DB - PRIME DP - Unbound Medicine ER -
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