4.8 Article

Synthesis of Silacyclohexanones from Divinylsilanes and Allylamines by a Rh-Catalyzed Cyclization

Journal

ORGANIC LETTERS
Volume 24, Issue 2, Pages 726-730

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c04183

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Funding

  1. National Natural Science Foundation of China [21921002, 22171191]
  2. Open Research Fund of Chengdu University of Traditional Chinese Medicine Key Laboratory of Systematic Research of Distinctive Chinese Medicine Resources in Southwest China [2020LF2003]
  3. Science and Technology Department of Sichuan Province [2020YFS0186]

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An efficient synthesis of silacyclohexanones with different silyl substituents has been developed using a [Rh(coe)(2)Cl](2)/PCy3 catalyst, which can be further oxidized to form silacyclohexadienones and transformed into silicon analogs of 2-deoxystreptamine or exo-alkylidenesilacyclohexadienes.
An efficient synthesis of silacyclohexanones bearing a variety of silyl substituents has been developed by a [Rh(coe)(2)Cl](2)/PCy3-catalyzed cyclization of divinylsilanes with Jun's allylamine. The silacyclohexanones can be oxidized with DDQ to give the corresponding silacyclohexadienones, which are further transformed into silicon analog of 2-deoxystreptamine or exo-alkylidenesilacyclohexadienes.

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