Asymmetric Construction of Tertiary/Secondary Carbon–Phosphorus Bonds via Bifunctional Phosphonium Salt Catalyzed 1,6-Addition

ACS Catalysis ◽  
2021 ◽  
pp. 14168-14180
Author(s):  
Yuan Chen ◽  
Zhaoyuan Yu ◽  
Zhiyu Jiang ◽  
Jian-Ping Tan ◽  
Jia-Hong Wu ◽  
...  
Keyword(s):  
Phosphonium Salt ◽  
Secondary Carbon

Synthesis of 8-HEPE and 10-HDoHE in both (R)- and (S)-Forms via Wittig Reactions with COOH-Ylides

Synlett ◽  
2019 ◽  
Vol 30 (03) ◽  
pp. 338-342
Author(s):  
Yuta Suganuma ◽  
Shun Saito ◽  
Yuichi Kobayashi
Keyword(s):  
Docosahexaenoic Acid ◽  
Eicosapentaenoic Acid ◽  
Wittig Reaction ◽  
Phosphonium Salt ◽  
Wittig Reactions

Wittig reactions using carboxy (CO2H) ylides derived from a carboxylic phosphonium salt and NaN(TMS)2 (NaHMDS) in a 1:1 ratio were applied to the synthesis of 8-HEPE and 10-HDoHE, which are metabolites of eicosapentaenoic acid and docosahexaenoic acid, respectively. The attempted Wittig reaction of 3-(TBS-oxy)pentadeca-4E,6Z,9Z,12Z-tetraenal with the carboxy ylide (2 equiv) derived from Br– Ph3P+(CH2)4CO2H and NaHMDS (1:1) competed with the elimination of the TBS-oxy group at C3 to give a mixture of the Wittig product and the elimination product in 45–50% and 30–40% yields, respectively. The elimination was suppressed completely by using three equiv of the carboxy ylides in THF/HMPA (7–8:1), and the subsequent desilylation gave 8-HEPE in (R)- and (S)-forms. Similarly, both enantiomers of 10-HDoHE were synthesized.

scholarly journals Plasma‐Assisted Immobilization of a Phosphonium Salt and Its Use as a Catalyst in the Valorization of CO 2

ChemSusChem ◽  
2020 ◽  
Vol 13 (7) ◽  
pp. 1825-1833 ◽  
Author(s):  
Yuya Hu ◽  
Sandra Peglow ◽  
Lars Longwitz ◽  
Marcus Frank ◽  
Jan Dirk Epping ◽  
...  
Keyword(s):  
Phosphonium Salt

scholarly journals Design of bifunctional quaternary phosphonium salt catalysts for CO2 fixation reaction with epoxides under mild conditions

2016 ◽  
Vol 18 (17) ◽  
pp. 4611-4615 ◽  
Author(s):  
Shiyao Liu ◽  
Naoki Suematsu ◽  
Keiji Maruoka ◽  
Seiji Shirakawa
Keyword(s):  
Co2 Fixation ◽  
Phosphonium Salt ◽  
Cyclic Carbonates ◽  
Efficient Synthesis ◽  
Reaction Conditions ◽  
Mild Conditions ◽  
Phosphonium Iodide ◽  
Fixation Reaction ◽  
Quaternary Phosphonium Salt

An efficient synthesis of cyclic carbonates from epoxides and CO2 under mild reaction conditions was achieved via the use of a designed bifunctional quaternary phosphonium iodide catalyst.

scholarly journals Intermolecular Rhodium-Catalysed Hydroamination of Non-Activated Olefins: Effect of Olefin, Amine, Phosphine and Phosphonium Salt

ChemPlusChem ◽  
2012 ◽  
Vol 77 (6) ◽  
pp. 445-454 ◽  
Author(s):  
Mireia Rodriguez-Zubiri ◽  
Christine Baudequin ◽  
Aurélien Béthegnies ◽  
Jean-Jacques Brunet
Keyword(s):  
Phosphonium Salt ◽  
Activated Olefins

Thermal and Photocontrol of the Equilibrium between a 2-Phosphinoazobenzene and an Inner Phosphonium Salt

2005 ◽  
Vol 127 (34) ◽  
pp. 11954-11955 ◽  
Author(s):  
Masaki Yamamura ◽  
Naokazu Kano ◽  
Takayuki Kawashima
Keyword(s):  
Phosphonium Salt
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