VAPOL phosphoric acid catalysis: the highly enantioselective addition of imides to imines

2007 ◽  
pp. 4477 ◽  
Author(s):  
Yuxue Liang ◽  
Emily B. Rowland ◽  
Gerald B. Rowland ◽  
Jason A. Perman ◽  
Jon C. Antilla
Keyword(s):  
Phosphoric Acid ◽  
Acid Catalysis ◽  
Enantioselective Addition

ChemInform Abstract: VAPOL Phosphoric Acid Catalysis: The Highly Enantioselective Addition of Imides to Imines.

ChemInform ◽  
2008 ◽  
Vol 39 (11) ◽  
Author(s):  
Yuxue Liang ◽  
Emily B. Rowland ◽  
Gerald B. Rowland ◽  
Jason A. Perman ◽  
Jon C. Antilla
Keyword(s):  
Phosphoric Acid ◽  
Acid Catalysis ◽  
Enantioselective Addition

Practical catalytic enantioselective synthesis of 2,3-dihydroquin-azolinones by chiral brønsted acid catalysis

2021 ◽  
Author(s):  
Yongbiao Guo ◽  
Zhenhua Gao ◽  
Junchen Li ◽  
Xiaojing Bi ◽  
Enxue Shi ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Acid Catalysis ◽  
Enantioselective Synthesis ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Brönsted Acid ◽  
Chiral Bronsted Acid ◽  
Bronsted Acid Catalysis

An efficient, practical and scalable protocol to prepare chiral 2,3-dihydroquinazolinones was developed under catalysis of spirocyclic SPINOL-phosphoric acid.

The Highly Enantioselective Addition of Indoles toN-Acyl Imines with Use of a Chiral Phosphoric Acid Catalyst

2007 ◽  
Vol 9 (14) ◽  
pp. 2609-2611 ◽  
Author(s):  
Gerald B. Rowland ◽  
Emily B. Rowland ◽  
Yuxue Liang ◽  
Jason A. Perman ◽  
Jon C. Antilla
Keyword(s):  
Phosphoric Acid ◽  
Acid Catalyst ◽  
Chiral Phosphoric Acid ◽  
Enantioselective Addition

Asymmetric C-H and N-H functionalization of Indoles involving Central Chirality via Chiral Phosphoric Acid Catalysis

2021 ◽  
Vol 18 ◽  
Author(s):  
Alemayehu Gashaw ◽  
Dereje Kebebew Debeli ◽  
Meseret Chemeda
Keyword(s):  
Phosphoric Acid ◽  
Organic Compounds ◽  
Organic Synthesis ◽  
Acid Catalysis ◽  
Bond Formation ◽  
Acid Catalysts ◽  
Asymmetric Syntheses ◽  
Chiral Phosphoric Acid ◽  
Great Progress ◽  
Interesting Area

: The C-H and N-H functionalization of indoles is an interesting area of research that has a useful impact on organic synthesis due to the availability of chiral indole scaffolds in the discovery of drugs, synthetic bioactive compounds, and natural products. The chiral phosphoric acid catalysts (CPAs) have proven to be a powerful and versatile class of enantioselective organocatalysts. Many asymmetric syntheses of organic compounds have been carried out with these catalysts in C–C and C-N bond formation reactions, and great progress has been reported. By 2011, several reviews were published covering some important topics and recent achievements in this field. Therefore, in this review, the most recent advances, research breakthroughs with key examples involving mechanisms of CPA-catalyzed C-H and N-H functionalization of indoles to form central chirality via Friedel Crafts, Michael type, and rearrangement reactions were reviewed and reported.

scholarly journals Organocatalytic enantioselective dearomatization of thiophenes by 1,10-conjugate addition of indole imine methides

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Xingguang Li ◽  
Meng Duan ◽  
Peiyuan Yu ◽  
K. N. Houk ◽  
Jianwei Sun
Keyword(s):  
Hydrogen Bonding ◽  
Phosphoric Acid ◽  
Nucleophilic Addition ◽  
Acid Catalysis ◽  
Conjugate Addition ◽  
Mild Conditions ◽  
Rapid Construction ◽  
Chiral Phosphoric Acid ◽  
Cyclic Molecules ◽  
Selectivity Control

AbstractCatalytic asymmetric dearomatization (CADA) is a powerful tool for the rapid construction of diverse chiral cyclic molecules from cheap and easily available arenes. This work reports an organocatalytic enantioselective dearomatization of substituted thiophenes in the context of a rare remote asymmetric 1,10-conjugate addition. By suitable stabilization of the thiophenyl carbocation with an indole motif in the form of indole imine methide, excellent remote chemo-, regio-, and stereocontrol in the nucleophilic addition can be achieved with chiral phosphoric acid catalysis under mild conditions. This protocol can be successfully extended to the asymmetric dearomatization of other heteroarenes including selenophenes and furans. Control experiments and DFT calculations demonstrate a possible pathway in which hydrogen bonding plays an important role in selectivity control.

Chiral phosphoric acid catalyzed enantioselective addition of thiols to in situ generated ketimines: Synthesis of N , S -ketals

2017 ◽  
Vol 58 (2) ◽  
pp. 145-151 ◽  
Author(s):  
Rajshekhar A. Unhale ◽  
Nagaraju Molleti ◽  
Nirmal K. Rana ◽  
Sivasankaran Dhanasekaran ◽  
Subhrajyoti Bhandary ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Chiral Phosphoric Acid ◽  
Acid Catalyzed ◽  
Enantioselective Addition
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