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An Efficient, Practical, and Enantioselective Method for Synthesis of Homoallenylamides Catalyzed by an Aminoalcohol-Derived, Boron-Based Catalyst

[Image: see text] A practical catalytic method for enantioselective addition of an allene unit to aldimines is disclosed. Transformations are promoted by an in-situ-generated B-based catalyst that is derived from a simple, robust, and readily accessible (in multigram quantities) chiral aminoalcohol....

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Autores principales: Wu, Hao, Haeffner, Fredrik, Hoveyda, Amir H.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3985786/
https://www.ncbi.nlm.nih.gov/pubmed/24588835
http://dx.doi.org/10.1021/ja500374p
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author Wu, Hao
Haeffner, Fredrik
Hoveyda, Amir H.
author_facet Wu, Hao
Haeffner, Fredrik
Hoveyda, Amir H.
author_sort Wu, Hao
collection PubMed
description [Image: see text] A practical catalytic method for enantioselective addition of an allene unit to aldimines is disclosed. Transformations are promoted by an in-situ-generated B-based catalyst that is derived from a simple, robust, and readily accessible (in multigram quantities) chiral aminoalcohol. A range of aryl-, heteroaryl-, and alkyl-substituted homoallenylamides can be obtained in 66–91% yield and 84:16 to >99:1 enantiomeric ratio through reactions performed at ambient temperature and in the presence of 0.1–3.0 mol% of the chiral catalyst and a commercially available allenylboron reagent. The catalytic protocol does not require strict anhydrous conditions, can be performed on gram scale, and promotes highly selective addition of an allenyl unit (vs a propargyl group). The utility of the approach is demonstrated through development of succinct approaches to syntheses of anisomycin and epi-cytoxazone.
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spelling pubmed-39857862015-03-03 An Efficient, Practical, and Enantioselective Method for Synthesis of Homoallenylamides Catalyzed by an Aminoalcohol-Derived, Boron-Based Catalyst Wu, Hao Haeffner, Fredrik Hoveyda, Amir H. J Am Chem Soc [Image: see text] A practical catalytic method for enantioselective addition of an allene unit to aldimines is disclosed. Transformations are promoted by an in-situ-generated B-based catalyst that is derived from a simple, robust, and readily accessible (in multigram quantities) chiral aminoalcohol. A range of aryl-, heteroaryl-, and alkyl-substituted homoallenylamides can be obtained in 66–91% yield and 84:16 to >99:1 enantiomeric ratio through reactions performed at ambient temperature and in the presence of 0.1–3.0 mol% of the chiral catalyst and a commercially available allenylboron reagent. The catalytic protocol does not require strict anhydrous conditions, can be performed on gram scale, and promotes highly selective addition of an allenyl unit (vs a propargyl group). The utility of the approach is demonstrated through development of succinct approaches to syntheses of anisomycin and epi-cytoxazone. American Chemical Society 2014-03-03 2014-03-12 /pmc/articles/PMC3985786/ /pubmed/24588835 http://dx.doi.org/10.1021/ja500374p Text en Copyright © 2014 American Chemical Society
spellingShingle Wu, Hao
Haeffner, Fredrik
Hoveyda, Amir H.
An Efficient, Practical, and Enantioselective Method for Synthesis of Homoallenylamides Catalyzed by an Aminoalcohol-Derived, Boron-Based Catalyst
title An Efficient, Practical, and Enantioselective Method for Synthesis of Homoallenylamides Catalyzed by an Aminoalcohol-Derived, Boron-Based Catalyst
title_full An Efficient, Practical, and Enantioselective Method for Synthesis of Homoallenylamides Catalyzed by an Aminoalcohol-Derived, Boron-Based Catalyst
title_fullStr An Efficient, Practical, and Enantioselective Method for Synthesis of Homoallenylamides Catalyzed by an Aminoalcohol-Derived, Boron-Based Catalyst
title_full_unstemmed An Efficient, Practical, and Enantioselective Method for Synthesis of Homoallenylamides Catalyzed by an Aminoalcohol-Derived, Boron-Based Catalyst
title_short An Efficient, Practical, and Enantioselective Method for Synthesis of Homoallenylamides Catalyzed by an Aminoalcohol-Derived, Boron-Based Catalyst
title_sort efficient, practical, and enantioselective method for synthesis of homoallenylamides catalyzed by an aminoalcohol-derived, boron-based catalyst
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3985786/
https://www.ncbi.nlm.nih.gov/pubmed/24588835
http://dx.doi.org/10.1021/ja500374p
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