ChemInform Abstract: Assembly of the Southern Macrocyclic Half of (+)-Spirastrellolide A (V) Through Cyclic Acetal Tethered Ring-Closing Metathesis and 1,3-anti-Mukaiyama-aldol.

ChemInform ◽  
2013 ◽  
Vol 44 (18) ◽  
pp. no-no
Author(s):  
Yu Tang ◽  
Jin-Haek Yang ◽  
Jia Liu ◽  
Chao-Chao Wang ◽  
Ming-Can Lv ◽  
...  
Keyword(s):  
Cyclic Acetal ◽  
Ring Closing Metathesis ◽  
Spirastrellolide A ◽  
Mukaiyama Aldol

ASSEMBLY OF THE SOUTHERN MACROCYCLIC HALF OF (+)-SPIRASTRELLOLIDE A THROUGH CYCLIC ACETAL TETHERED RING-CLOSING METATHESIS AND 1,3-ANTI-MUKAIYAMA-ALDOL

Heterocycles ◽  
2012 ◽  
Vol 86 (1) ◽  
pp. 565 ◽  
Author(s):  
Richard P. Hsung ◽  
Yu Tang ◽  
Jin-Haek Yang ◽  
Jia Liu ◽  
Chao-Chao Wang ◽  
...  
Keyword(s):  
Cyclic Acetal ◽  
Ring Closing Metathesis ◽  
Spirastrellolide A ◽  
Mukaiyama Aldol

Convergent Total Synthesis of (+)-TMC-151C by a Vinylogous Mukaiyama Aldol Reaction and Ring-Closing Metathesis

2010 ◽  
Vol 50 (3) ◽  
pp. 680-683 ◽  
Author(s):  
Ryosuke Matsui ◽  
Kentaro Seto ◽  
Yuna Sato ◽  
Takahiro Suzuki ◽  
Atsuo Nakazaki ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Aldol Reaction ◽  
Ring Closing Metathesis ◽  
Mukaiyama Aldol Reaction ◽  
Mukaiyama Aldol

Convergent Total Synthesis of (+)-TMC-151C by a Vinylogous Mukaiyama Aldol Reaction and Ring-Closing Metathesis

2010 ◽  
Vol 123 (3) ◽  
pp. 706-709 ◽  
Author(s):  
Ryosuke Matsui ◽  
Kentaro Seto ◽  
Yuna Sato ◽  
Takahiro Suzuki ◽  
Atsuo Nakazaki ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Aldol Reaction ◽  
Ring Closing Metathesis ◽  
Mukaiyama Aldol Reaction ◽  
Mukaiyama Aldol

Mukaiyama Aldol Reaction Catalyzed by (Benz)imidazolium-Based Halogen Bond Donors

2020 ◽  
Author(s):  
Revannath L. Sutar ◽  
Nikita Erochok ◽  
Stefan Huber
Keyword(s):  
Halogen Bond ◽  
Aldol Reaction ◽  
Mukaiyama Aldol Reaction ◽  
Mukaiyama Aldol ◽  
Background Reaction ◽  
Strong Performance ◽  
The Stability ◽  
Elemental Iodine

A series of cationic monodentate and bidentate iodo(benz)­imidazolium-based halogen bond (XB) donors were employed as catalysts in a Mukaiyama aldol reaction. While 5 mol% of a monodentate variant showed noticeable activity, a <i>syn</i>-preorganized bidentate XB donor provided a strong performance even with 0.5 mol% loading. In contrast to the very active BAr<sup>F</sup><sub>4</sub> salts, PF<sub>6</sub> or OTf salts were either inactive or showed background reaction. Repetition experiments clearly ruled out a potential hidden catalysis by elemental iodine and demonstrated the stability of our catalyst over three consecutive cycles.

Nickel-Catalyzed Inter- and Intramolecular Carbon-Sulfur Bond Metathesis by Reversible Arylation

2019 ◽  
Author(s):  
Tristan Delcaillau ◽  
Alessandro Bismuto ◽  
Zhong Lian ◽  
Bill Morandi
Keyword(s):  
Good Yield ◽  
Functional Group ◽  
Product Formation ◽  
Single Bond ◽  
Ring Closing Metathesis ◽  
Catalytic Systems ◽  
Metathesis Reactions ◽  
New Applications ◽  
Further Development ◽  
Sulfur Bond

A nickel-catalyzed carbon-sulfur bond metathesis has been developed to access high-value thioethers. 1,2-bis(dicyclohexylphosphino)ethane (dcype) is essential to promote this highly functional group tolerant reaction. Further, synthetically challenging macrocycles could be obtained in good yield in an unusual example of ring-closing metathesis which does not involve alkene bonds. In-depth organometallic studies support a reversible Ni(0)-Ni(II) pathway to product formation. Overall, this work does not only disclose a more sustainable and more functional group tolerant alternative to previous catalytic systems based on Pd, but also presents new applications and mechanistic information which are highly relevant to the further development and application of unusual single bond metathesis reactions.

One-Pot Tandem Ring-Opening and Ring-Closing Metathesis Polymerization of Disubstituted Cyclopentenes Featuring a Terminal Alkyne Functionality

2020 ◽  
Vol 53 (11) ◽  
pp. 4330-4337
Author(s):  
Santhosh Kumar Podiyanachari ◽  
Salvador Moncho ◽  
Edward N. Brothers ◽  
Saeed Al-Meer ◽  
Mohammed Al-Hashimi ◽  
...  
Keyword(s):  
Ring Opening ◽  
Terminal Alkyne ◽  
Ring Closing Metathesis ◽  
One Pot ◽  
Metathesis Polymerization

Synthesis of coumarins by ring-closing metathesis using Grubbs’ catalyst

2003 ◽  
Vol 44 (22) ◽  
pp. 4199-4201 ◽  
Author(s):  
Tuyen Nguyen Van ◽  
Silvia Debenedetti ◽  
Norbert De Kimpe
Keyword(s):  
Ring Closing Metathesis ◽  
Grubbs Catalyst

New pseudohalide ligands in Ru-catalyzed olefin metathesis — A robust, air-activated iminopyrrolato catalyst

2005 ◽  
Vol 83 (6-7) ◽  
pp. 748-754 ◽  
Author(s):  
Samantha D Drouin ◽  
Heather M Foucault ◽  
Glenn PA Yap ◽  
Deryn E Fogg
Keyword(s):  
Key Words ◽  
Olefin Metathesis ◽  
High Reactivity ◽  
Ring Closing Metathesis ◽  
Grubbs Catalyst ◽  
X Ray ◽  
X Ray Crystallography

Reaction of the Grubbs catalyst RuCl2(PCy3)2(CHPh) (1) with lithium 2-[(2,6-diisopropylphenyl)imino]pyrrolide·Et2O (LiNN′·Et2O) gives alkylidene complex 5, containing a chelating, σ-bound iminopyrrolato unit. The structure of 5 is confirmed by X-ray crystallography. Treatment of 5 with pyridine generates RuCl(NN′)(py)2(CHPh) (6) via displacement of PCy3. Complex 5 effects ring-closing metathesis in air, displaying high reactivity relative to 6.Key words: ruthenium, alkylidene, metathesis, pyrrolimine, iminopyrrolato.

Hydrosilylation and Mukaiyama Aldol-type Reactions of Imine and Quinoline Derivatives Catalyzed by a Mesoionic Carbene-Stabilized Borenium Ion

2021 ◽  
Author(s):  
Joshua J. Clarke ◽  
Karthik Devaraj ◽  
Brian Bestvater ◽  
Ryoto Kojima ◽  
Patrick Eisenberger ◽  
...  
Keyword(s):  
Room Temperature ◽  
Secondary Amines ◽  
Catalyst Loading ◽  
Quinoline Derivatives ◽  
Mukaiyama Aldol

Aldimines and ketimines containing electron-donating and electron-withdrawing groups can be hydrosilylated with borenium catalysts at as low as 1 mol% catalyst loading at room temperature, providing the corresponding secondary amines...

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