scholarly journals Chiral phosphine-mediated intramolecular [3 + 2] annulation: enhanced enantioselectivity by achiral Brønsted acid

2017 ◽  
Vol 8 (7) ◽  
pp. 5196-5200 ◽  
Author(s):  
Weijun Yao ◽  
Zhaoyuan Yu ◽  
Shan Wen ◽  
Huanzhen Ni ◽  
Nisar Ullah ◽  
...  

Enantioselective intramolecular [3 + 2] annulation of chalcone–allenes catalyzed by amino acid-derived phosphines and achiral Brønsted acids has been developed.

Author(s):  
Dion B. Nemez ◽  
Baldeep K. Sidhu ◽  
Patrick K. Giesbrecht ◽  
Jason D. Braun ◽  
David E. Herbert

A convenient electrochemical methodology for the hydrogenation of benzoxazinones and aryl-substituted α-ketoester substrates is presented, using carbon electrodes and sustainable Brønsted acids.


2019 ◽  
Vol 17 (38) ◽  
pp. 8690-8694 ◽  
Author(s):  
Minglei Yuan ◽  
Ifenna I. Mbaezue ◽  
Zhi Zhou ◽  
Filip Topic ◽  
Youla S. Tsantrizos

An intramolecular H-bond in the Brønsted acid OttoPhosa I accelerates the reaction and increases enantioselectivity for the transfer hydrogenation of quinolines.


2020 ◽  
Vol 16 ◽  
pp. 88-105
Author(s):  
Katarzyna Włodarczyk ◽  
Piotr Borowski ◽  
Marek Stankevič

β-Hydroxyalkylphosphine sulfides undergo [1,3]- or [1,4]-sulfur atom phosphorus-to-carbon migration in the presence of Lewis or Brønsted acids. The direction of sulfur atom migration depends on the type of acid used for the reaction. In the presence of a Brønsted acid, mainly [1,3]-rearrangement is observed, whereas a Lewis acid catalyzes the [1,4]-sulfur migration. To gain insight into the mechanism of these transformations, the stereochemistry of these rearrangements have been tested, along with the conduction of some control experiments and DFT calculations.


2019 ◽  
Vol 92 (2) ◽  
pp. 203-209 ◽  
Author(s):  
Danijel Glavač ◽  
Ivanka Jerić ◽  
Matija Gredičak

An organocatalytic interrupted three-component Ugi reaction for the synthesis of α,α–diaryl α–amino acid derivatives is described. The transformation proceeds with a range of isocyanides and 3-aryl isoindolinone alcohols using Brønsted acid catalysts to afford products in good to excellent yields. Based on the obtained results, a reaction mechanism is proposed and discussed.


2017 ◽  
Vol 46 (18) ◽  
pp. 5901-5910 ◽  
Author(s):  
Khatera Hazin ◽  
Spencer C. Serin ◽  
Brian O. Patrick ◽  
Maria B. Ezhova ◽  
Derek P. Gates

The development of solid, weighable Brønsted acids featuring the hexacoordinated phosphorous(v) anion [TRISPHAT]− are reported.


SynOpen ◽  
2017 ◽  
Vol 01 (01) ◽  
pp. 0011-0014
Author(s):  
Yukihiro Arakawa ◽  
Takahiro Kohda ◽  
Keiji Minagawa ◽  
Yasushi Imada

Aerobic reduction of olefins with hydrazine was proven to be efficiently catalysed by readily available Brønsted acids, such as p-tolu­enesulfonic acid monohydrate, providing hydrogenated products in very good yields and chemoselectivity under mild conditions.


2017 ◽  
Vol 15 (31) ◽  
pp. 6474-6477 ◽  
Author(s):  
Jianjun Li ◽  
Yiwei Fu ◽  
Cong Qin ◽  
Yang Yu ◽  
Hao Li ◽  
...  

A mild and efficient asymmetric cyclization reaction catalyzed by chiral Brønsted acids has been developed for the synthesis of chiral isoquinolinonaphthyridines.


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