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Diastereoselective Synthesis of Highly Substituted Tetrahydrofurans by Pd-Catalyzed Tandem Oxidative Cyclization-Redox Relay Reactions Controlled by Intramolecular Hydrogen Bonding

Brooks, Joshua L ; Xu, Liping ; Wiest, Olaf ; Tan, Derek S

The Journal of organic chemistry, 06 January 2017, Vol.82(1), pp.57-75 [Tạp chí có phản biện]

E-ISSN: 1520-6904 ; PMID: 28004933 Version:1 ; DOI: 10.1021/acs.joc.6b02053

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  • Nhan đề:
    Diastereoselective Synthesis of Highly Substituted Tetrahydrofurans by Pd-Catalyzed Tandem Oxidative Cyclization-Redox Relay Reactions Controlled by Intramolecular Hydrogen Bonding
  • Tác giả: Brooks, Joshua L ; Xu, Liping ; Wiest, Olaf ; Tan, Derek S
  • Chủ đề: Furans -- Chemical Synthesis ; Palladium -- Chemistry
  • Là 1 phần của: The Journal of organic chemistry, 06 January 2017, Vol.82(1), pp.57-75
  • Mô tả: Palladium-catalyzed oxidative cyclization of alkenols provides a convenient entry into cyclic ethers but typically proceeds with little or no diastereoselectivity for cyclization of trisubstituted olefins to form tetrahydrofurans due to the similar energies of competing 5-membered transition-state conformations. Herein, a new variant of this reaction has been developed in which a PdCl/1,4-benzoquinone catalyst system coupled with introduction of a hydrogen-bond acceptor in the substrate enhances both diastereoselectivity and reactivity. Cyclization occurs with 5-exo Markovnikov regioselectivity. Mechanistic and computational studies support an anti-oxypalladation pathway in which intramolecular hydrogen bonding increases the nucleophilicity of the alcohol and enforces conformational constraints that enhance diastereoselectivity. The cyclization is followed by a tandem redox-relay process that provides versatile side-chain functionalities for further derivatization.
  • Ngôn ngữ: English
  • Số nhận dạng: E-ISSN: 1520-6904 ; PMID: 28004933 Version:1 ; DOI: 10.1021/acs.joc.6b02053

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