Synthesis of Trisubstituted Alkenes via Olefin Cross-Metathesis

1999 ◽  
Vol 1 (11) ◽  
pp. 1751-1753 ◽  
Author(s):  
Arnab K. Chatterjee ◽  
Robert H. Grubbs
Keyword(s):  
Cross Metathesis ◽  
Trisubstituted Alkenes

scholarly journals A Relay Strategy Actuates Pre-Existing Trisubstituted Olefins in Monoterpenoids to Form New Trisubstituted Olefins by Cross Metathesis

2019 ◽  
Author(s):  
Karim Bahou ◽  
D. Christopher Braddock ◽  
Adam G. Meyer ◽  
G. Paul Savage ◽  
Zhensheng Shi ◽  
...  
Keyword(s):  
Geometrical Isomer ◽  
Successful Implementation ◽  
Enantiomerically Pure ◽  
Cross Metathesis ◽  
Trisubstituted Olefins ◽  
The Cross ◽  
Trisubstituted Alkenes

<b><u>Abstract:</u></b> A retrosynthetic disconnection-reconnection analysis of epoxypolyenes – substrates that can undergo cyclization to podocarpane-type tricycles – reveals relay-actuated Δ<sup>6,7</sup>-functionalized monoterpenoid alcohols for ruthenium benzylidene catalyzed olefin cross metathesis with homoprenyl benzenes. Successful implementation of this approach provided several epoxypolyenes as expected (<i>E</i>:<i>Z</i>, ca. 2-3:1). The method is further generalized for the cross metathesis of pre-existing trisubstituted olefins in other relay-actuated Δ<sup>6,7</sup>-functionalized monoterpenoid alcohols with various other trisubstituted alkenes to form new trisubstituted olefins. Epoxypolyene cyclization of an enantiomerically pure, but geometrically impure, epoxypolyene substrate provides an enantiomerically pure, trans-fused, podocarpane-type tricycle (from the <i>E</i>-geometrical isomer).<br>

scholarly journals A Relay Strategy Actuates Pre-Existing Trisubstituted Olefins in Monoterpenoids for Cross-Metathesis with Trisubstituted Alkenes

2020 ◽  
Vol 85 (7) ◽  
pp. 4906-4917 ◽  
Author(s):  
Karim A. Bahou ◽  
D. Christopher Braddock ◽  
Adam G. Meyer ◽  
G. Paul Savage ◽  
Zhensheng Shi ◽  
...  
Keyword(s):  
Cross Metathesis ◽  
Trisubstituted Olefins ◽  
Trisubstituted Alkenes

scholarly journals Synthesis of E- and Z-trisubstituted alkenes by catalytic cross-metathesis

Nature ◽  
2017 ◽  
Vol 552 (7685) ◽  
pp. 347-354 ◽  
Author(s):  
Thach T. Nguyen ◽  
Ming Joo Koh ◽  
Tyler J. Mann ◽  
Richard R. Schrock ◽  
Amir H. Hoveyda
Keyword(s):  
Cross Metathesis ◽  
Trisubstituted Alkenes

ChemInform Abstract: Synthesis of Trisubstituted Alkenes via Olefin Cross-Metathesis.

ChemInform ◽  
2010 ◽  
Vol 31 (8) ◽  
pp. no-no
Author(s):  
Arnab K. Chatterjee ◽  
Robert H. Grubbs
Keyword(s):  
Cross Metathesis ◽  
Trisubstituted Alkenes

A Relay Strategy Actuates Pre-Existing Trisubstituted Olefins in Monoterpenoids to Form New Trisubstituted Olefins by Cross Metathesis

2019 ◽  
Author(s):  
Karim Bahou ◽  
D. Christopher Braddock ◽  
Adam G. Meyer ◽  
G. Paul Savage ◽  
Zhensheng Shi ◽  
...  
Keyword(s):  
Geometrical Isomer ◽  
Successful Implementation ◽  
Enantiomerically Pure ◽  
Cross Metathesis ◽  
Trisubstituted Olefins ◽  
The Cross ◽  
Trisubstituted Alkenes

<b><u>Abstract:</u></b> A retrosynthetic disconnection-reconnection analysis of epoxypolyenes – substrates that can undergo cyclization to podocarpane-type tricycles – reveals relay-actuated Δ<sup>6,7</sup>-functionalized monoterpenoid alcohols for ruthenium benzylidene catalyzed olefin cross metathesis with homoprenyl benzenes. Successful implementation of this approach provided several epoxypolyenes as expected (<i>E</i>:<i>Z</i>, ca. 2-3:1). The method is further generalized for the cross metathesis of pre-existing trisubstituted olefins in other relay-actuated Δ<sup>6,7</sup>-functionalized monoterpenoid alcohols with various other trisubstituted alkenes to form new trisubstituted olefins. Epoxypolyene cyclization of an enantiomerically pure, but geometrically impure, epoxypolyene substrate provides an enantiomerically pure, trans-fused, podocarpane-type tricycle (from the <i>E</i>-geometrical isomer).<br>

Endgroup and Sidechain Functionalization of Surface-Initiated ROMP Thin Films: Progress Towards ROMP-Based Molecular Wires

2018 ◽  
Author(s):  
Nicholas Marshall
Keyword(s):  
Thin Films ◽  
Contact Angle ◽  
Cyclic Voltammetry ◽  
Polymer Films ◽  
Conjugated Polymer ◽  
Ring Opening ◽  
Molecular Wires ◽  
Metathesis Polymerization ◽  
Cross Metathesis ◽  
Active Ester

A set of experiments in surface-initiated ring-opening metathesis polymerization, including end-functionalization of growing brushes and contact angle/cyclic voltammetry measurements. We report preparation and CV of two different conjugated polymer films, and several endgroup and sidechain functionalization experiments using cross-metathesis and active ester substitution.<br>

Synthesis of Conjugated Triynes via Alkyne Metathesis

2019 ◽  
Author(s):  
Idriss Curbet ◽  
Sophie Colombel-Rouen ◽  
Romane Manguin ◽  
Anthony Clermont ◽  
Alexandre Quelhas ◽  
...  
Keyword(s):  
Steric Hindrance ◽  
High Selectivity ◽  
Alkyne Metathesis ◽  
Cross Metathesis ◽  
Synthetic Strategy ◽  
Sterically Hindered ◽  
Site Selective

<div> <div> <div> <div> <p>The synthesis of conjugated triynes by molybdenum-catalyzed alkyne metathesis is reported. Strategic to the success of this approach is the utilization of sterically-hindered diynes that allowed for the site- selective alkyne metathesis to produce the desired con- jugated triyne products. The steric hindrance of alkyne moiety was found to be crucial in preventing the for- mation of diyne byproducts. This novel synthetic strategy was amenable to self- and cross-metathesis providing straightforward access to the corresponding symmetrical and dissymmetrical triynes with high selectivity. </p> </div> </div> </div> </div>

Concise Total Synthesis of Curvulone B

Synlett ◽  
2020 ◽  
Author(s):  
Debendra K. Mohapatra ◽  
Shivalal Banoth ◽  
Utkal Mani Choudhury ◽  
Kanakaraju Marumudi ◽  
Ajit C. Kunwar
Keyword(s):  
Total Synthesis ◽  
Stereoselective Synthesis ◽  
Ring System ◽  
Bond Forming ◽  
Cross Metathesis ◽  
Bond Forming Reactions ◽  
Key Steps

AbstractA concise and convergent stereoselective synthesis of curvulone B is described. The synthesis utilized a tandem isomerization followed by C–O and C–C bond-forming reactions following Mukaiyama-type aldol conditions for the construction of the trans-2,6-disubstituted dihydropyran ring system as the key steps. Other important features of this synthesis are a cross-metathesis, epimerization, and Friedel–Crafts acylation.

scholarly journals Conversion of Dinitrogen into Nitrile: Cross Metathesis of N2‐Derived Molybdenum Nitride with Alkynes

2021 ◽  
Author(s):  
Jinyi Song ◽  
Qian LIAO ◽  
Xin Hong ◽  
Li Jin ◽  
Nicolas Mézailles
Keyword(s):  
Molybdenum Nitride ◽  
Cross Metathesis
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