Cyclization of nonterminal alkynic β-Keto esters catalyzed by gold(I) complex with a semihollow, end-capped triethynylphosphine ligand

Hideto Ito, Yusuke Makida, Atsuko Ochida, Hirohisa Ohmiya, Masaya Sawamura

Research output: Contribution to journalArticle

50 Citations (Scopus)

Abstract

(Chemical Equation Presented) 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.

Original languageEnglish
Pages (from-to)5051-5054
Number of pages4
JournalOrganic Letters
Volume10
Issue number21
DOIs
Publication statusPublished - Dec 1 2008

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Cyclization
Gold
esters
Esters
gold
Ligands
ligands
Carbon
carbon
Substrates
products
triethynylphosphine

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Cyclization of nonterminal alkynic β-Keto esters catalyzed by gold(I) complex with a semihollow, end-capped triethynylphosphine ligand. / Ito, Hideto; Makida, Yusuke; Ochida, Atsuko; Ohmiya, Hirohisa; Sawamura, Masaya.

In: Organic Letters, Vol. 10, No. 21, 01.12.2008, p. 5051-5054.

Research output: Contribution to journalArticle

Ito, Hideto ; Makida, Yusuke ; Ochida, Atsuko ; Ohmiya, Hirohisa ; Sawamura, Masaya. / Cyclization of nonterminal alkynic β-Keto esters catalyzed by gold(I) complex with a semihollow, end-capped triethynylphosphine ligand. In: Organic Letters. 2008 ; Vol. 10, No. 21. pp. 5051-5054.
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AU - Sawamura, Masaya

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