Ruthenium catalyzed cycloisomerization of silicon-tethered 1,7-enynes to give exocyclic 1,3-dienes

Lauren Kaminsky; Daniel A. Clark

doi:10.1021/ol5026926

Ruthenium catalyzed cycloisomerization of silicon-tethered 1,7-enynes to give exocyclic 1,3-dienes

Lauren Kaminsky, Daniel A. Clark

Department of Chemistry

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

19 Scopus citations

Abstract

The cycloisomerization of vinyl silicon-tethered 1,7-enynes has been accomplished using catalytic Cp∗Ru(COD)Cl. The products possess a new silane moiety and trisubstituted alkenes as part of the diene system. The reaction scope includes aryl, alkyl, vinyl, and cyclopropyl alkyne functionalities. Silicon was found not to be a mandatory component of the tether. The utility of the products was demonstrated through manipulation of the vinyl silane and Diels-Alder chemistry. (Chemical Equation Presented).

Original language	English (US)
Pages (from-to)	5450-5453
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	20
DOIs	https://doi.org/10.1021/ol5026926
State	Published - Oct 17 2014

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol5026926

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title = "Ruthenium catalyzed cycloisomerization of silicon-tethered 1,7-enynes to give exocyclic 1,3-dienes",

abstract = "The cycloisomerization of vinyl silicon-tethered 1,7-enynes has been accomplished using catalytic Cp∗Ru(COD)Cl. The products possess a new silane moiety and trisubstituted alkenes as part of the diene system. The reaction scope includes aryl, alkyl, vinyl, and cyclopropyl alkyne functionalities. Silicon was found not to be a mandatory component of the tether. The utility of the products was demonstrated through manipulation of the vinyl silane and Diels-Alder chemistry. (Chemical Equation Presented).",

author = "Lauren Kaminsky and Clark, {Daniel A.}",

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AU - Kaminsky, Lauren

AU - Clark, Daniel A.

PY - 2014/10/17

Y1 - 2014/10/17

N2 - The cycloisomerization of vinyl silicon-tethered 1,7-enynes has been accomplished using catalytic Cp∗Ru(COD)Cl. The products possess a new silane moiety and trisubstituted alkenes as part of the diene system. The reaction scope includes aryl, alkyl, vinyl, and cyclopropyl alkyne functionalities. Silicon was found not to be a mandatory component of the tether. The utility of the products was demonstrated through manipulation of the vinyl silane and Diels-Alder chemistry. (Chemical Equation Presented).

AB - The cycloisomerization of vinyl silicon-tethered 1,7-enynes has been accomplished using catalytic Cp∗Ru(COD)Cl. The products possess a new silane moiety and trisubstituted alkenes as part of the diene system. The reaction scope includes aryl, alkyl, vinyl, and cyclopropyl alkyne functionalities. Silicon was found not to be a mandatory component of the tether. The utility of the products was demonstrated through manipulation of the vinyl silane and Diels-Alder chemistry. (Chemical Equation Presented).

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JF - Organic Letters

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Ruthenium catalyzed cycloisomerization of silicon-tethered 1,7-enynes to give exocyclic 1,3-dienes

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