scholarly journals Organocatalytic asymmetric selenofunctionalization of tryptamine for the synthesis of hexahydropyrrolo[2,3-b]indole derivatives

2013 ◽  
Vol 9 ◽  
pp. 1559-1564 ◽  
Author(s):  
Qiang Wei ◽  
Ya-Yi Wang ◽  
Yu-Liu Du ◽  
Liu-Zhu Gong
Keyword(s):  
Phosphoric Acid ◽  
Indole Derivatives ◽  
Chiral Phosphoric Acid ◽  
Acid Catalyzed ◽  
High Yields

A chiral phosphoric acid-catalyzed selenofunctionalization of tryptamine derivatives provides access to 3a-(phenylselenyl)-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole derivatives in high yields and with synthetically useful levels of enantioselectivity (up to 89% ee).

Enantioselective Biginelli Reaction of Aliphatic Aldehydes Catalyzed by a Chiral Phosphoric Acid: A Key Step in the Synthesis of the Bicyclic Guanidine Core of Crambescin A and Batzelladine A

Synthesis ◽  
2018 ◽  
Vol 50 (12) ◽  
pp. 2394-2406 ◽  
Author(s):  
Yongbiao Guo ◽  
Chuanpin Zou ◽  
Zhenhua Gao ◽  
Chongxu Fan ◽  
Jisheng Chen ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Biginelli Reaction ◽  
Aliphatic Aldehydes ◽  
Formal Synthesis ◽  
Chiral Phosphoric Acid ◽  
Wide Range ◽  
Synthetic Utility ◽  
Acid Catalyzed ◽  
High Yields ◽  
Optically Pure

An efficient chiral phosphoric acid catalyzed Biginelli reaction for the synthesis of optically pure 4-alkyl-3,4-dihydropyrimidin-2-(1H)-ones has been developed, with a wide range of the desired products being obtained in moderate to high yields with good to excellent enantioselectivities (up to >99% ee after one recrystallization). The synthetic utility of this reaction is illustrated in various aliphatic bicyclic guanidine compounds, which is applied in the formal synthesis of the bicyclic guanidine core of crambescin A and batzelladine A.

Chiral Phosphoric Acid Catalyzed Stereoselective Spiroketalizations

Synlett ◽  
2013 ◽  
Vol 24 (06) ◽  
pp. 661-665 ◽  
Author(s):  
Pavel Nagorny ◽  
Zhankui Sun ◽  
Grace Winschel
Keyword(s):  
Phosphoric Acid ◽  
Chiral Phosphoric Acid ◽  
Acid Catalyzed

scholarly journals Catalytic Enantioselective Synthesis of 4-Amino-1,2,3,4-tetrahydropyridine Derivatives from Intramolecular Nucleophilic Addition Reaction of Tertiary Enamides

Synlett ◽  
2018 ◽  
Vol 30 (04) ◽  
pp. 483-487 ◽  
Author(s):  
Shuo Tong ◽  
Mei-Xiang Wang
Keyword(s):  
Phosphoric Acid ◽  
Asymmetric Catalysis ◽  
Nucleophilic Addition ◽  
Addition Reaction ◽  
Enantioselective Synthesis ◽  
Chiral Phosphoric Acid ◽  
Substrate Engineering ◽  
Nucleophilic Addition Reaction ◽  
Engineering Strategy ◽  
Acid Catalyzed

A general and efficient method for the synthesis of highly enantiopure 4-amino-1,2,3,4-tetradydropyridine derivatives based on chiral phosphoric acid catalyzed intramolecular nucleophilic addition of tertiary enamides to imines has been developed. We have also demonstrated a substrate engineering strategy to significantly improve the enantioselectivity of asymmetric catalysis

scholarly journals Organocatalytic Asymmetric [2 + 4] Cycloadditions of 3-Vinylindoles with ortho-Quinone Methides

Molecules ◽  
2021 ◽  
Vol 26 (21) ◽  
pp. 6751
Author(s):  
Si-Jia Liu ◽  
Man-Su Tu ◽  
Kai-Yue Liu ◽  
Jia-Yi Chen ◽  
Shao-Fei Ni ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Structural Diversity ◽  
Quinone Methides ◽  
Chiral Phosphoric Acid ◽  
Catalytic Asymmetric ◽  
High Yields ◽  
Asymmetric Cycloadditions

Catalytic asymmetric [2 + 4] cycloadditions of 3-vinylindoles with ortho-quinone methides and their precursors were carried out in the presence of chiral phosphoric acid to afford a series of indole-containing chroman derivatives with structural diversity in overall high yields (up to 98%), good diastereoselectivities (up to 93:7 dr) and moderate to excellent enantioselectivities (up to 98% ee). This approach not only enriches the chemistry of catalytic asymmetric cycloadditions involving 3-vinylindoles but is also useful for synthesizing chiral chroman derivatives.

Sign in / Sign up

Export Citation Format

Share Document