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

doi:10.1021/ol802079r

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 journal › Article › peer-review

26 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 language	English
Pages (from-to)	5051-5054
Number of pages	4
Journal	Organic letters
Volume	10
Issue number	21
DOIs	https://doi.org/10.1021/ol802079r
Publication status	Published - 2008
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol802079r

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

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.",

author = "Hideto Ito and Yusuke Makida and Atsuko Ochida and Hirohisa Ohmiya and Masaya Sawamura",

year = "2008",

doi = "10.1021/ol802079r",

language = "English",

volume = "10",

pages = "5051--5054",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

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T1 - Cyclization of nonterminal alkynic β-Keto esters catalyzed by gold(I) complex with a semihollow, end-capped triethynylphosphine ligand

AU - Ito, Hideto

AU - Makida, Yusuke

AU - Ochida, Atsuko

AU - Ohmiya, Hirohisa

AU - Sawamura, Masaya

PY - 2008

Y1 - 2008

N2 - (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.

AB - (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.

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DO - 10.1021/ol802079r

M3 - Article

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AN - SCOPUS:60949085568

SN - 1523-7060

VL - 10

SP - 5051

EP - 5054

JO - Organic Letters

JF - Organic Letters

IS - 21

ER -

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

Abstract

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