Enantioselective synthesis of hexahydrofuro[3,2-c] quinolines through a multicatalytic and multicomponent process. A new “aromatic sandwich” model for BINOL-phosphoric acid catalyzed reactions

2014 ◽  
Vol 5 (3) ◽  
pp. 996-1007 ◽  
Author(s):  
Jonás Calleja ◽  
Adán B. González-Pérez ◽  
Ángel R. de Lera ◽  
Rosana Álvarez ◽  
Francisco J. Fañanás ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Enantioselective Synthesis ◽  
Acid Catalyzed ◽  
Catalyzed Reactions ◽  
Sandwich Model

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

Highly Diastereo- and Enantioselective Synthesis of Cyclohepta[b ]indoles by Chiral-Phosphoric-Acid-Catalyzed (4+3) Cycloaddition

2018 ◽  
Vol 130 (37) ◽  
pp. 12297-12301 ◽  
Author(s):  
Coralie Gelis ◽  
Guillaume Levitre ◽  
Jérémy Merad ◽  
Pascal Retailleau ◽  
Luc Neuville ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Enantioselective Synthesis ◽  
Chiral Phosphoric Acid ◽  
Acid Catalyzed

scholarly journals Salutaridine and its derivatives as thebaine-equivalents in the synthesis of aporphines

2013 ◽  
Vol 11 (12) ◽  
pp. 2022-2030 ◽  
Author(s):  
Antal Udvardy ◽  
Attila Sipos
Keyword(s):  
Enantioselective Synthesis ◽  
Acid Catalyzed ◽  
Catalyzed Reactions

AbstractHere we report the transformation of tetracyclic morphinan salutaridine (1) into 2,3,10,11-tetrasubstituted (R)-aporphines. This method serves as another chemical proof of the previously verified biosynthetic connection with pentacyclic morphinan-6,8-diene-type thebaine. In the presence of nucleophiles, this procedure could lead to pharmacologically interesting new tetrasubstituted aporphinoids. The enantioselective synthesis of 7S-salutaridinol (2) has been also achieved in order to investigate the acid-catalyzed reactions of this natural morphinan.

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