Reactivity of Stabilized Vinyldiazo Compounds toward Alkenyl- and Alkynylsilanes under Gold Catalysis: Regio- and Stereoselective Synthesis of Skipped Dienes and Enynes

[Image: see text] We report the gold-catalyzed reaction of vinyldiazo compounds and alkenylsilanes to produce skipped dienes, which are common structural motifs in an array of bioactive compounds. This carbon–carbon bond-forming transformation proceeds with complete regio- and stereoselectivity with...

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Autores principales: Bernardo, Olaya, Yamamoto, Kota, Fernández, Israel, López, Luis A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8900156/
https://www.ncbi.nlm.nih.gov/pubmed/33983038
http://dx.doi.org/10.1021/acs.orglett.1c01381
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author Bernardo, Olaya
Yamamoto, Kota
Fernández, Israel
López, Luis A.
author_facet Bernardo, Olaya
Yamamoto, Kota
Fernández, Israel
López, Luis A.
author_sort Bernardo, Olaya
collection PubMed
description [Image: see text] We report the gold-catalyzed reaction of vinyldiazo compounds and alkenylsilanes to produce skipped dienes, which are common structural motifs in an array of bioactive compounds. This carbon–carbon bond-forming transformation proceeds with complete regio- and stereoselectivity with the silyl group serving as a regio- and stereocontrolling element. Likewise, the use of alkynylsilanes as reaction partners yielded skipped enynes resulting from a C(sp)–C(sp(3)) coupling. Mechanistic experiments and DFT studies have provided support for a stepwise mechanism.
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spelling pubmed-89001562022-03-08 Reactivity of Stabilized Vinyldiazo Compounds toward Alkenyl- and Alkynylsilanes under Gold Catalysis: Regio- and Stereoselective Synthesis of Skipped Dienes and Enynes Bernardo, Olaya Yamamoto, Kota Fernández, Israel López, Luis A. Org Lett [Image: see text] We report the gold-catalyzed reaction of vinyldiazo compounds and alkenylsilanes to produce skipped dienes, which are common structural motifs in an array of bioactive compounds. This carbon–carbon bond-forming transformation proceeds with complete regio- and stereoselectivity with the silyl group serving as a regio- and stereocontrolling element. Likewise, the use of alkynylsilanes as reaction partners yielded skipped enynes resulting from a C(sp)–C(sp(3)) coupling. Mechanistic experiments and DFT studies have provided support for a stepwise mechanism. American Chemical Society 2021-05-13 2021-06-04 /pmc/articles/PMC8900156/ /pubmed/33983038 http://dx.doi.org/10.1021/acs.orglett.1c01381 Text en © 2021 American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Bernardo, Olaya
Yamamoto, Kota
Fernández, Israel
López, Luis A.
Reactivity of Stabilized Vinyldiazo Compounds toward Alkenyl- and Alkynylsilanes under Gold Catalysis: Regio- and Stereoselective Synthesis of Skipped Dienes and Enynes
title Reactivity of Stabilized Vinyldiazo Compounds toward Alkenyl- and Alkynylsilanes under Gold Catalysis: Regio- and Stereoselective Synthesis of Skipped Dienes and Enynes
title_full Reactivity of Stabilized Vinyldiazo Compounds toward Alkenyl- and Alkynylsilanes under Gold Catalysis: Regio- and Stereoselective Synthesis of Skipped Dienes and Enynes
title_fullStr Reactivity of Stabilized Vinyldiazo Compounds toward Alkenyl- and Alkynylsilanes under Gold Catalysis: Regio- and Stereoselective Synthesis of Skipped Dienes and Enynes
title_full_unstemmed Reactivity of Stabilized Vinyldiazo Compounds toward Alkenyl- and Alkynylsilanes under Gold Catalysis: Regio- and Stereoselective Synthesis of Skipped Dienes and Enynes
title_short Reactivity of Stabilized Vinyldiazo Compounds toward Alkenyl- and Alkynylsilanes under Gold Catalysis: Regio- and Stereoselective Synthesis of Skipped Dienes and Enynes
title_sort reactivity of stabilized vinyldiazo compounds toward alkenyl- and alkynylsilanes under gold catalysis: regio- and stereoselective synthesis of skipped dienes and enynes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8900156/
https://www.ncbi.nlm.nih.gov/pubmed/33983038
http://dx.doi.org/10.1021/acs.orglett.1c01381
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