Synthesis of Substituted Indolizidines and Quinolizidines by Regioselective Intramolecular Modified Julia Olefination of Imides

2019 ◽  
Vol 85 (2) ◽  
pp. 864-875 ◽  
Author(s):  
Bastien Raison ◽  
Nicolas Dussart ◽  
Laura Levy ◽  
Peter G. Goekjian ◽  
David Gueyrard
Keyword(s):  
Julia Olefination

Synthetic and Mechanistic Studies of a Versatile Heteroaryl Thioether Directing Group for Pd(II) Catalysis

2019 ◽  
Author(s):  
Andrew Romine ◽  
Kin Yang ◽  
Malkanthi Karunananda ◽  
Jason Chen ◽  
Keary Engle
Keyword(s):  
Mechanistic Studies ◽  
Salvianolic Acid ◽  
Wide Range ◽  
Computational Data ◽  
Synthetic Utility ◽  
Directing Group ◽  
High Yields ◽  
Julia Olefination ◽  
Reaction Progress Kinetic Analysis

A weakly coordinating monodentate heteroaryl thioether directing group has been developed for use in Pd(II) catalysis to orchestrate key elementary steps in the catalytic cycle that require conformational flexibility in a manner that is difficult to accomplish with traditional strongly coordinating directing groups. This benzothiazole thioether, (BT)S, directing group can be used to promote oxidative Heck reactivity of internal alkenes providing a wide range of products in moderate to high yields. To demonstrate the broad applicability of this directing group, arene C–H olefination was also successfully developed. Reaction progress kinetic analysis provides insights into the role of the directing group in each reaction, which is supplemented with computational data for the oxidative Heck reaction. Furthermore, this (BT)S directing group can be transformed into a number of synthetically useful functional groups, including a sulfone for Julia olefination, allowing it to serve as a “masked olefin” directing group in synthetic planning. In order to demonstrate this synthetic utility, natural products (+)-salvianolic acid A and salvianolic acid F are formally synthesized using the (BT)S directed C–H olefination as the key step.

Synthesis of substituted exo-glucals via a modified Julia olefination and identification as selective β-glucosidase inhibitors

2014 ◽  
Vol 12 (4) ◽  
pp. 690-699 ◽  
Author(s):  
Samuel Habib ◽  
Florent Larnaud ◽  
Emmanuel Pfund ◽  
Teresa Mena Barragán ◽  
Thierry Lequeux ◽  
...  
Keyword(s):  
Glucosidase Inhibitors ◽  
Julia Olefination

Straightforward synthesis of fucoxanthin short-chain derivatives via modified-Julia olefination

2014 ◽  
Vol 55 (2) ◽  
pp. 407-410 ◽  
Author(s):  
Satoshi Okumura ◽  
Takayuki Kajikawa ◽  
Koki Yano ◽  
Kazuhiko Sakaguchi ◽  
Daisuke Kosumi ◽  
...  
Keyword(s):  
Short Chain ◽  
Julia Olefination

scholarly journals Synthesis of Chiral, Enantiopure Allylic Amines by the Julia Olefination of α-Amino Esters

Molecules ◽  
2016 ◽  
Vol 21 (6) ◽  
pp. 805
Author(s):  
Fabio Benedetti ◽  
Federico Berti ◽  
Lidia Fanfoni ◽  
Michele Garbo ◽  
Giorgia Regini ◽  
...  
Keyword(s):  
Allylic Amines ◽  
Amino Esters ◽  
Julia Olefination

Esterase-sensitive sulfur dioxide prodrugs inspired by modified Julia olefination

2017 ◽  
Vol 53 (73) ◽  
pp. 10124-10127 ◽  
Author(s):  
Wenyi Wang ◽  
Binghe Wang
Keyword(s):  
Sulfur Dioxide ◽  
Release Rates ◽  
Tunable Release ◽  
Julia Olefination

Esterase-triggered SO2prodrugs with tunable release rates.

Synthesis of 4-Nitrophenyl Sulfones and Application in the Modified Julia Olefination

Synlett ◽  
2006 ◽  
Vol 2006 (08) ◽  
pp. 1255-1259 ◽  
Author(s):  
Jieping Zhu ◽  
Daniela Mirk ◽  
Jean-Marie Grassot
Keyword(s):  
Julia Olefination

Synthesis of Methylene Exoglycals Using a Modified Julia Olefination

Synlett ◽  
2005 ◽  
pp. 520-522 ◽  
Author(s):  
David Gueyrard ◽  
Rose Haddoub ◽  
Amine Salem ◽  
Nassib Said Bacar ◽  
Peter G. Goekjian
Keyword(s):  
Julia Olefination

Efficient Synthesis of Substituted Vinyl Ethers Using the Julia Olefination

2003 ◽  
Vol 5 (25) ◽  
pp. 4851-4854 ◽  
Author(s):  
Simon Surprenant ◽  
Wing Yan Chan ◽  
Carl Berthelette
Keyword(s):  
Efficient Synthesis ◽  
Vinyl Ethers ◽  
Julia Olefination

Synthesis of Fluorinated and Trifluoromethyl-Substituted Alkenes through the Modified Julia Olefination: An Update

Synthesis ◽  
2015 ◽  
Vol 47 (11) ◽  
pp. 1534-1546 ◽  
Author(s):  
Emmanuel Pfund ◽  
Thierry Lequeux ◽  
David Gueyrard
Keyword(s):  
Large Range ◽  
Short Review ◽  
The Novel ◽  
Smiles Rearrangement ◽  
Julia Olefination

The modified Julia olefination is now a powerful tool for the synthesis of a large range of functionalized alkenes. This short review covers the last five years and provides an overview of the synthesis of mono-, difluoro-, and trifluoromethyl-substituted alkenes via the modified Julia olefination focusing on the novel scope of this reaction.1 Introduction2 Monofluoroalkenes2.1 Disubstituted α- and β-Monofluoroalkenes2.2 Bis(trifluoromethyl)phenyl Sulfones2.3 Conjugated Monofluoroalkenes2.4 Intramolecular Julia Olefination2.5 Smiles Rearrangement from Fluorinated Keto Sulfones2.6 Fluoroallylamines2.7 Fluorinated exo-Glycals2.8 Monofluoroalkenes with an α-Stereocenter at the Allylic Position3 1,1-Difluoroalkenes4 Trifluoromethyl-Substituted Alkenes5 Conclusion

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