Diastereoselective oxidative carbon-carbon bond formation via silyl bis-enol ethers

Christopher T. Avetta; Leah C. Konkol; Carla N. Taylor; Karen C. Dugan; Charlotte L. Stern; Regan J. Thomson

doi:10.1021/ol802516z

Diastereoselective oxidative carbon-carbon bond formation via silyl bis-enol ethers

Christopher T. Avetta^*, Leah C. Konkol, Carla N. Taylor, Karen C. Dugan, Charlotte L. Stern, Regan J. Thomson

^*Corresponding author for this work

Chemistry

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

57 Scopus citations

Abstract

(Chemical Equation Presented) Diisopropylsilyl bis-enol ethers are shown to be powerful intermediates for the diastereoselective dimerization and cross-coupling of cyclic ketones. The trends observed for the oxidative coupling of a range of different dialkylsilyl bis-enol ethers derived from cyclohexanone are rationalized by invoking a stereochemical model based on a Thorpe-Ingold effect.

Original language	English (US)
Pages (from-to)	5621-5624
Number of pages	4
Journal	Organic Letters
Volume	10
Issue number	24
DOIs	https://doi.org/10.1021/ol802516z
State	Published - 2008

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol802516z

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title = "Diastereoselective oxidative carbon-carbon bond formation via silyl bis-enol ethers",

abstract = "(Chemical Equation Presented) Diisopropylsilyl bis-enol ethers are shown to be powerful intermediates for the diastereoselective dimerization and cross-coupling of cyclic ketones. The trends observed for the oxidative coupling of a range of different dialkylsilyl bis-enol ethers derived from cyclohexanone are rationalized by invoking a stereochemical model based on a Thorpe-Ingold effect.",

author = "Avetta, {Christopher T.} and Konkol, {Leah C.} and Taylor, {Carla N.} and Dugan, {Karen C.} and Stern, {Charlotte L.} and Thomson, {Regan J.}",

year = "2008",

doi = "10.1021/ol802516z",

language = "English (US)",

volume = "10",

pages = "5621--5624",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "24",

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TY - JOUR

T1 - Diastereoselective oxidative carbon-carbon bond formation via silyl bis-enol ethers

AU - Avetta, Christopher T.

AU - Konkol, Leah C.

AU - Taylor, Carla N.

AU - Dugan, Karen C.

AU - Stern, Charlotte L.

AU - Thomson, Regan J.

PY - 2008

Y1 - 2008

N2 - (Chemical Equation Presented) Diisopropylsilyl bis-enol ethers are shown to be powerful intermediates for the diastereoselective dimerization and cross-coupling of cyclic ketones. The trends observed for the oxidative coupling of a range of different dialkylsilyl bis-enol ethers derived from cyclohexanone are rationalized by invoking a stereochemical model based on a Thorpe-Ingold effect.

AB - (Chemical Equation Presented) Diisopropylsilyl bis-enol ethers are shown to be powerful intermediates for the diastereoselective dimerization and cross-coupling of cyclic ketones. The trends observed for the oxidative coupling of a range of different dialkylsilyl bis-enol ethers derived from cyclohexanone are rationalized by invoking a stereochemical model based on a Thorpe-Ingold effect.

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UR - http://www.scopus.com/inward/citedby.url?scp=60949089799&partnerID=8YFLogxK

U2 - 10.1021/ol802516z

DO - 10.1021/ol802516z

M3 - Article

C2 - 19053737

AN - SCOPUS:60949089799

SN - 1523-7060

VL - 10

SP - 5621

EP - 5624

JO - Organic Letters

JF - Organic Letters

IS - 24

ER -

Diastereoselective oxidative carbon-carbon bond formation via silyl bis-enol ethers

Abstract

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CCDC 704633: Experimental Crystal Structure Determination

CCDC 704637: Experimental Crystal Structure Determination

CCDC 704635: Experimental Crystal Structure Determination

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Diastereoselective oxidative carbon-carbon bond formation via silyl bis-enol ethers

Abstract

ASJC Scopus subject areas

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Datasets

CCDC 704633: Experimental Crystal Structure Determination

CCDC 704637: Experimental Crystal Structure Determination

CCDC 704635: Experimental Crystal Structure Determination

Cite this