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Cyclization of Nonterminal Alkynic β-Keto Esters Catalyzed by Gold(I) Complex with a Semihollow, End-Capped Triethynylphosphine Ligand

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    Cyclization of Nonterminal Alkynic β-Keto Esters Catalyzed by Gold(I) Complex with a Semihollow, End-Capped Triethynylphosphine Ligand
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    Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060-0810, Japan
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    Organic Letters

    Cite this: Org. Lett. 2008, 10, 21, 5051–5054
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    https://doi.org/10.1021/ol802079r
    Published October 15, 2008
    Copyright © 2008 American Chemical Society
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    Abstract

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    A cationic gold(I) complex with a semihollow-shaped trialkynylphosphine catalyzed 5-exo-dig and 6-endo-dig cyclizations of various internal alkynic β-keto esters, showing a marked advantage over a gold(I)−PPh3 complex with respect to the rates of the reactions and the product yields. It is proposed that the gold-bound alkynic substrate in a catalytic pocket must be somewhat folded and that such a steric effect makes the carbon−carbon bond formation entropically more favorable.

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    60. Hideto Ito, Yusuke Makida, Atsuko Ochida, Hirohisa Ohmiya, Masaya Sawamura. ChemInform Abstract: Cyclization of Nonterminal Alkynic β‐Keto Esters Catalyzed by Gold(I) Complex with a Semihollow, End‐Capped Triethynylphosphine Ligand.. ChemInform 2009, 40 (12) https://doi.org/10.1002/chin.200912033
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    Organic Letters

    Cite this: Org. Lett. 2008, 10, 21, 5051–5054
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ol802079r
    Published October 15, 2008
    Copyright © 2008 American Chemical Society
    Request reuse permissions

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