Template-directed olefin cross metathesis

Stuart J. Cantrill; Robert H. Grubbs; Daniela Lanari; Ken C.F. Leung; Alshakim Nelson; Katherine G. Poulin-Kerstien; Sebastian P. Smidt; J. Fraser Stoddart; David A. Tirrell

doi:10.1021/ol051599g

Template-directed olefin cross metathesis

Stuart J. Cantrill, Robert H. Grubbs^*, Daniela Lanari, Ken C.F. Leung, Alshakim Nelson, Katherine G. Poulin-Kerstien, Sebastian P. Smidt, J. Fraser Stoddart, David A. Tirrell

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

44 Citations (Scopus)

Abstract

(Figure Presented) A template containing two secondary dialkylammonium ion recognition sites for encirclement by olefin-bearing dibenzo[24]crown-8 derivatives has been used to promote olefin cross metatheses with ruthenium-alkylidene catalysts. For monoolefin monomers, the rates of metatheses and yields of the dimers are both amplified in the presence of the template. Likewise, for a diolefin monomer, the yield of the dimer is enhanced in the presence of the template under conditions where higher oligomers are not formed.

Original language	English
Pages (from-to)	4213-4216
Number of pages	4
Journal	Organic Letters
Volume	7
Issue number	19
DOIs	https://doi.org/10.1021/ol051599g
Publication status	Published - 1 Sept 2005

Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol051599g

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@article{622928a30b674377a755bceb203a7d88,

title = "Template-directed olefin cross metathesis",

abstract = "(Figure Presented) A template containing two secondary dialkylammonium ion recognition sites for encirclement by olefin-bearing dibenzo[24]crown-8 derivatives has been used to promote olefin cross metatheses with ruthenium-alkylidene catalysts. For monoolefin monomers, the rates of metatheses and yields of the dimers are both amplified in the presence of the template. Likewise, for a diolefin monomer, the yield of the dimer is enhanced in the presence of the template under conditions where higher oligomers are not formed.",

author = "Cantrill, {Stuart J.} and Grubbs, {Robert H.} and Daniela Lanari and Leung, {Ken C.F.} and Alshakim Nelson and Poulin-Kerstien, {Katherine G.} and Smidt, {Sebastian P.} and Stoddart, {J. Fraser} and Tirrell, {David A.}",

note = "The authors thank the Office of Naval Research (ONR) for its support through the Multidisciplinary University Research Initiative (MURI) program, the Alexander von Humboldt Foundation for a Feodor Lynen postdoctoral fellowship to S.P.S., the Croucher Foundation (HKSAR) for a postdoctoral fellowship to K.C.-F.L., and the National Institutes of Health for a postdoctoral fellowship to A.N. ",

year = "2005",

month = sep,

day = "1",

doi = "10.1021/ol051599g",

language = "English",

volume = "7",

pages = "4213--4216",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "19",

}

TY - JOUR

T1 - Template-directed olefin cross metathesis

AU - Cantrill, Stuart J.

AU - Grubbs, Robert H.

AU - Lanari, Daniela

AU - Leung, Ken C.F.

AU - Nelson, Alshakim

AU - Poulin-Kerstien, Katherine G.

AU - Smidt, Sebastian P.

AU - Stoddart, J. Fraser

AU - Tirrell, David A.

N1 - The authors thank the Office of Naval Research (ONR) for its support through the Multidisciplinary University Research Initiative (MURI) program, the Alexander von Humboldt Foundation for a Feodor Lynen postdoctoral fellowship to S.P.S., the Croucher Foundation (HKSAR) for a postdoctoral fellowship to K.C.-F.L., and the National Institutes of Health for a postdoctoral fellowship to A.N.

PY - 2005/9/1

Y1 - 2005/9/1

N2 - (Figure Presented) A template containing two secondary dialkylammonium ion recognition sites for encirclement by olefin-bearing dibenzo[24]crown-8 derivatives has been used to promote olefin cross metatheses with ruthenium-alkylidene catalysts. For monoolefin monomers, the rates of metatheses and yields of the dimers are both amplified in the presence of the template. Likewise, for a diolefin monomer, the yield of the dimer is enhanced in the presence of the template under conditions where higher oligomers are not formed.

AB - (Figure Presented) A template containing two secondary dialkylammonium ion recognition sites for encirclement by olefin-bearing dibenzo[24]crown-8 derivatives has been used to promote olefin cross metatheses with ruthenium-alkylidene catalysts. For monoolefin monomers, the rates of metatheses and yields of the dimers are both amplified in the presence of the template. Likewise, for a diolefin monomer, the yield of the dimer is enhanced in the presence of the template under conditions where higher oligomers are not formed.

UR - http://www.scopus.com/inward/record.url?scp=25444472910&partnerID=8YFLogxK

U2 - 10.1021/ol051599g

DO - 10.1021/ol051599g

M3 - Journal article

C2 - 16146390

AN - SCOPUS:25444472910

SN - 1523-7060

VL - 7

SP - 4213

EP - 4216

JO - Organic Letters

JF - Organic Letters

IS - 19

ER -

Template-directed olefin cross metathesis

Abstract

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