Photogenerated acid-catalyzed formation of phosphonic/phosphoric acids by deprotection of esters

1994 ◽  
Author(s):  
Marcia L. Schilling ◽  
Howard E. Katz ◽  
Francis M. Houlihan ◽  
Janet M. Kometani ◽  
Susan M. Stein ◽  
...  
Keyword(s):  
Acid Catalyzed ◽  
Phosphoric Acids

Photogenerated Acid-Catalyzed Formation of Phosphonic/Phosphoric Acids by Deprotection of Esters in Polymer Films

1995 ◽  
Vol 28 (1) ◽  
pp. 110-115 ◽  
Author(s):  
Marcia L. Schilling ◽  
Howard E. Katz ◽  
Francis M. Houlihan ◽  
Janet M. Kometani ◽  
Susan M. Stein ◽  
...  
Keyword(s):  
Polymer Films ◽  
Acid Catalyzed ◽  
Phosphoric Acids

Chiral Phosphoric Acid-Catalyzed Enantioselective [4+3] Cyclization Reaction of 4-Indolylmethanols and Quinone Esters

Synlett ◽  
2021 ◽  
Author(s):  
Zhouli Chen ◽  
Lei Wang ◽  
Yiheng Qian ◽  
Xufeng Lin
Keyword(s):  
Phosphoric Acid ◽  
Cyclization Reaction ◽  
Reaction Conditions ◽  
Efficient Access ◽  
Single Diastereomer ◽  
Chiral Phosphoric Acid ◽  
Acid Catalyzed ◽  
Phosphoric Acids

An asymmetric [4+3] cyclization reaction of racemic 4-indolylmethanols and quinone esters catalyzed by chiral phosphoric acids has been developed. This method provides efficient access to biologically important benzoxepino[5,4,3-cd] indoles featuring both axial and central chirality in good yields with up to 98% ee and essentially single diastereomer in mild reaction conditions.

The control effects of different scaffolds in chiral phosphoric acids: a case study of enantioselective asymmetric arylation

2019 ◽  
Vol 9 (22) ◽  
pp. 6482-6491 ◽  
Author(s):  
Lihan Zhu ◽  
Hend Mohamed ◽  
Haiyan Yuan ◽  
Jingping Zhang
Keyword(s):  
Phosphoric Acid ◽  
Dft Calculations ◽  
Chiral Phosphoric Acid ◽  
Acid Catalyzed ◽  
Catalyzed Reactions ◽  
Phosphoric Acids

DFT calculations disclosed that the sign of enantioselectivity in chiral-phosphoric-acid catalyzed reactions can be tuned by BINOL- or SPINOL-derived backbones.

Secondary stereocontrolling interactions in chiral Brønsted acid catalysis: study of a Petasis–Ferrier-type rearrangement catalyzed by chiral phosphoric acids

2014 ◽  
Vol 5 (9) ◽  
pp. 3515-3523 ◽  
Author(s):  
Kyohei Kanomata ◽  
Yasunori Toda ◽  
Yukihiro Shibata ◽  
Masahiro Yamanaka ◽  
Seiji Tsuzuki ◽  
...  
Keyword(s):  
Hydrogen Bonds ◽  
Phosphoric Acid ◽  
Acid Catalysis ◽  
Computational Studies ◽  
Stacking Interactions ◽  
Π Stacking ◽  
Chiral Phosphoric Acid ◽  
Acid Catalyzed ◽  
Chiral Bronsted Acid ◽  
Phosphoric Acids

Guided by computational studies, the involvement of non-classical C–H⋯O hydrogen bonds and π–π stacking interactions were found to be crucial for high stereocontrol in a chiral phosphoric acid-catalyzed reaction.

Chiral phosphoric acid catalyzed enantioselective annulation of acyclic enecarbamates to in situ-generated ortho-quinone methides

2017 ◽  
Vol 15 (35) ◽  
pp. 7272-7276 ◽  
Author(s):  
Chandan Gharui ◽  
Shreya Singh ◽  
Subhas Chandra Pan
Keyword(s):  
Phosphoric Acid ◽  
Cycloaddition Reaction ◽  
Quinone Methides ◽  
Chiral Phosphoric Acid ◽  
Acid Catalyzed ◽  
Phosphoric Acids

The first organocatalytic asymmetric [4 + 2]-cycloaddition reaction between acyclic enecarbamates with in situ generated ortho-quinone methides has been developed using chiral phosphoric acids as catalysts.

Chiral Phosphoric Acid Catalyzed Regio- and Enantioselective Reactions of Functionalized Propargylic Alcohols

2022 ◽  
Author(s):  
Chenxiao Qian ◽  
Meiwen Liu ◽  
Jianwei Sun ◽  
Pengfei Li
Keyword(s):  
Phosphoric Acid ◽  
Asymmetric Reactions ◽  
Propargylic Alcohols ◽  
Chiral Phosphoric Acid ◽  
Wide Range ◽  
Enantioselective Reactions ◽  
Acid Catalyzed ◽  
Catalyzed Reactions ◽  
Phosphoric Acids

Propargylic alcohols have been known as useful substrates in a wide range of asymmetric reactions. Particularly, the chiral phosphoric acids (CPAs) catalyzed reactions of functionalized propargylic alcohols opened a robust...

Acid Catalyzed Furan Ring Transposition

10.1039/sp768 ◽  
2014 ◽  
Author(s):  
Jamsheena V. ◽  
Ravindra Phatake
Keyword(s):  
Furan Ring ◽  
Acid Catalyzed

Catalytic Carbonyl-Olefin Metathesis of Aliphatic Ketones: Iron(III) HomoDimers as Lewis Acidic Superelectrophiles

2018 ◽  
Author(s):  
Haley Albright ◽  
Paul S. Riehl ◽  
Christopher C. McAtee ◽  
Jolene P. Reid ◽  
Jacob R. Ludwig ◽  
...  
Keyword(s):  
Lewis Acid ◽  
Olefin Metathesis ◽  
Acid Activation ◽  
Lewis Acid Catalysts ◽  
Distinct Mode ◽  
Aliphatic Ketones ◽  
Carbon Carbon Bond ◽  
Metathesis Reactions ◽  
Acid Catalyzed

<div>Catalytic carbonyl-olefin metathesis reactions have recently been developed as a powerful tool for carbon-carbon bond</div><div>formation. However, currently available synthetic protocols rely exclusively on aryl ketone substrates while the corresponding aliphatic analogs remain elusive. We herein report the development of Lewis acid-catalyzed carbonyl-olefin ring-closing metathesis reactions for aliphatic ketones. Mechanistic investigations are consistent with a distinct mode of activation relying on the in situ formation of a homobimetallic singly-bridged iron(III)-dimer as the active catalytic species. These “superelectrophiles” function as more powerful Lewis acid catalysts that form upon association of individual iron(III)-monomers. While this mode of Lewis acid activation has previously been postulated to exist, it has not yet been applied in a catalytic setting. The insights presented are expected to enable further advancement in Lewis acid catalysis by building upon the activation principle of “superelectrophiles” and broaden the current scope of catalytic carbonyl-olefin metathesis reactions.</div>

Arylboronic Acid-Catalyzed C-Allylation of Unprotected Oximes

2019 ◽  
Author(s):  
Juha Siitonen ◽  
Padmanabha V. Kattamuri ◽  
Muhammed Yousufuddin ◽  
Laszlo Kurti
Keyword(s):  
Total Synthesis ◽  
Acid Catalysts ◽  
Mechanistic Studies ◽  
Arylboronic Acid ◽  
Synthetic Utility ◽  
Acid Catalyzed

Unprotected keto- and aldoximes are readily <i>C</i>-allylated with allyl diisopropyl boronate in the presence of arylboronic acid catalysts to yield highly-substituted <i>N</i>-alpha-secondary (2°) and tertiary (3°) hydroxylamines. The method’s synthetic utility is demonstrated with the total synthesis of the trace alkaloid <i>N</i>-methyl-euphococcine. Preliminary experimental and computational mechanistic studies point toward the formation of a boroxine as the active allylating species.<br>

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