Au(I)- and Pt(II)-catalyzed cycloetherification of ω-hydroxy propargylic esters

Jef K. De Brabander; Bo Liu; Mingxing Qian

doi:10.1021/ol8008107

Au(I)- and Pt(II)-catalyzed cycloetherification of ω-hydroxy propargylic esters

Jef K. De Brabander, Bo Liu, Mingxing Qian

Research output: Contribution to journal › Article › peer-review

59 Scopus citations

Abstract

(Chemical Equation Presented) Depending on the nature of the metal catalyst, ω-hydroxy propargylic acetates choose between alternative cycloetherification manifolds to produce functionalized heterocycles in high yields. AuCl catalyzes the formation of oxacyclic enol acetates, whereas [Cl₂Pt(CH₂CH₂)]₂ (Zeise's dimer) will induce a propargylic substitution via an unprecedented S _N2′-type allenic substitution from within a chelated square planar cationic Pt(II) complex.

Original language	English (US)
Pages (from-to)	2533-2536
Number of pages	4
Journal	Organic Letters
Volume	10
Issue number	12
DOIs	https://doi.org/10.1021/ol8008107
State	Published - 2008

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Au(I)- and Pt(II)-catalyzed cycloetherification of ω-hydroxy propargylic esters",

abstract = "(Chemical Equation Presented) Depending on the nature of the metal catalyst, ω-hydroxy propargylic acetates choose between alternative cycloetherification manifolds to produce functionalized heterocycles in high yields. AuCl catalyzes the formation of oxacyclic enol acetates, whereas [Cl2Pt(CH2CH2)]2 (Zeise's dimer) will induce a propargylic substitution via an unprecedented S N2′-type allenic substitution from within a chelated square planar cationic Pt(II) complex.",

author = "{De Brabander}, {Jef K.} and Bo Liu and Mingxing Qian",

year = "2008",

doi = "10.1021/ol8008107",

language = "English (US)",

volume = "10",

pages = "2533--2536",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

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T1 - Au(I)- and Pt(II)-catalyzed cycloetherification of ω-hydroxy propargylic esters

AU - De Brabander, Jef K.

AU - Liu, Bo

AU - Qian, Mingxing

PY - 2008

Y1 - 2008

N2 - (Chemical Equation Presented) Depending on the nature of the metal catalyst, ω-hydroxy propargylic acetates choose between alternative cycloetherification manifolds to produce functionalized heterocycles in high yields. AuCl catalyzes the formation of oxacyclic enol acetates, whereas [Cl2Pt(CH2CH2)]2 (Zeise's dimer) will induce a propargylic substitution via an unprecedented S N2′-type allenic substitution from within a chelated square planar cationic Pt(II) complex.

AB - (Chemical Equation Presented) Depending on the nature of the metal catalyst, ω-hydroxy propargylic acetates choose between alternative cycloetherification manifolds to produce functionalized heterocycles in high yields. AuCl catalyzes the formation of oxacyclic enol acetates, whereas [Cl2Pt(CH2CH2)]2 (Zeise's dimer) will induce a propargylic substitution via an unprecedented S N2′-type allenic substitution from within a chelated square planar cationic Pt(II) complex.

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U2 - 10.1021/ol8008107

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JO - Organic Letters

JF - Organic Letters

IS - 12

ER -

Au(I)- and Pt(II)-catalyzed cycloetherification of ω-hydroxy propargylic esters

Abstract

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