Design of Chiral Bis-phosphoric Acid Catalyst Derived from (R)-3,3′-Di(2-hydroxy-3-arylphenyl)binaphthol: Catalytic Enantioselective Diels–Alder Reaction of α,β-Unsaturated Aldehydes with Amidodienes

2011 ◽  
Vol 133 (48) ◽  
pp. 19294-19297 ◽  
Author(s):  
Norie Momiyama ◽  
Tohru Konno ◽  
Yuichi Furiya ◽  
Takeaki Iwamoto ◽  
Masahiro Terada
Keyword(s):  
Phosphoric Acid ◽  
Acid Catalyst ◽  
Alder Reaction ◽  
Diels Alder ◽  
Unsaturated Aldehydes ◽  
Diels Alder Reaction

Asymmetric synthesis of isoquinuclidines by Diels–Alder reaction of 1,2-dihydropyridine utilizing a chiral Lewis acid catalyst

Tetrahedron ◽  
2012 ◽  
Vol 68 (6) ◽  
pp. 1774-1781 ◽  
Author(s):  
Chigusa Seki ◽  
Masafumi Hirama ◽  
N.D.M. Romauli Hutabarat ◽  
Junko Takada ◽  
Chonticha Suttibut ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Lewis Acid ◽  
Acid Catalyst ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Chiral Lewis Acid ◽  
Lewis Acid Catalyst

Design of chiral tin(IV) aryloxide as a mild Lewis acid catalyst for enantioselective Diels–Alder reaction

2006 ◽  
Vol 47 (6) ◽  
pp. 873-875 ◽  
Author(s):  
Taichi Kano ◽  
Teppei Konishi ◽  
Shunsuke Konishi ◽  
Keiji Maruoka
Keyword(s):  
Lewis Acid ◽  
Acid Catalyst ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Lewis Acid Catalyst

Synthesis of endo-fused 5-unsubstituted hexahydro-2H-pyrano[3,2- c]quinolines via sequential Sc(OTf)3-catalyzed cationic imino-Diels-Alder Reaction/N-debenzylation using N-benzylanilines, 3,4-dihydro-2H-pyran and paraformaldehyde under MW irradiation

2021 ◽  
Vol 18 ◽  
Author(s):  
Arturo René Mendoza Salgado ◽  
Carlos Eduardo Puerto Galvis ◽  
Vladimir V. Kouznetsov ◽  
Carlos Mario Meléndez
Keyword(s):  
Efficient Method ◽  
Cycloaddition Reaction ◽  
Acid Catalyst ◽  
Alder Reaction ◽  
Diels Alder ◽  
Synthetic Methods ◽  
Diels Alder Reaction ◽  
Catalytic Transfer ◽  
Lewis Acid Catalyst ◽  
Mw Irradiation

Background: Hexahydro-2H-pyrano[3,2-c]quinolines are known to have antibacterial, antifungal, and antitumor properties. Great efforts have been made to develop new synthetic methods that lead to the synthesis of valuable libraries. Extensive methodologies, low yields, excessive amounts of catalyst and expensive reactants are some of the limitations of current methodologies. Aim and Objective: Developing a useful and efficient method to construct diversely substituted hexahydro-2H-pyrano[3,2- c]quinolines into good to excellent yields through a cationic imino-Diels-Alder/N-debenzylation methodology. Method: The cationic imino-Diels-Alder/N-debenzylation methodology was used for the preparation of substituted hexahydro-2H-pyrano[3,2-c]quinolines. It involves the use of Sc(OTf)3 for activation of cationic imino-Diels-Alder cycloaddition reaction of N-benzylanilines, 3,4-dihydro-2H-pyran and paraformaldehyde in MeCN; and microwave irradiation to shorten reaction time to afford new 6-benzyl-hexahydro-2H-pyrano[3,2-c]quinolines whose catalytic transfer debenzylation reactions with HCO2NH4 in the presence of Pd/C (10%) and methanol give the new 5-unsubstituted pyrano[3,2- c]quinolines in excellent yields. Results: We found that optimal conditions for the preparation of hexahydro-2H-pyrano[3,2-c]quinolines were Sc(OTf)3 0,5 % and acetonitrile at 160 ° C for 15 min; and using paraformaldehyde obtained the 6-benzyl-hexahydro-2H-pyrano [3,2- c]quinolines with excellent yields, while the N-debenzylation process using ammonium formate in the presence of Pd/C and methanol resulted in the synthesis of hexahydro-2H-pyrano [3,2-c] quinolines with quantitative yields (95-98%). Conclusion: We describe an efficient method to synthesize hexahydro-2H-pyrano[3,2-c]quinolines via the cationic iminoDiels-Alder/N-debenzylation methodology using Sc(OTf)3 0,5 % as Lewis Acid catalyst. Excellent yields of the products, using of MW irradiation, short times of reactions and an efficient and highly diversified method are some of the main advantages of this new protocol.

scholarly journals Enantioselective Diels–Alder reaction of anthracene by chiral tritylium catalysis

2019 ◽  
Vol 15 ◽  
pp. 1304-1312 ◽  
Author(s):  
Qichao Zhang ◽  
Jian Lv ◽  
Sanzhong Luo
Keyword(s):  
Lewis Acid ◽  
Acid Catalyst ◽  
Alder Reaction ◽  
Ion Pair ◽  
Diels Alder ◽  
Highly Active ◽  
Diels Alder Reaction ◽  
New Type ◽  
Lewis Acid Catalyst ◽  
Trityl Cation

The combination of the trityl cation and a chiral weakly coordinating Fe(III)-based bisphosphate anion was used to develop a new type of a highly active carbocation Lewis acid catalyst. The stereocontrol potential of the chiral tritylium ion pair was demonstrated by its application in an enantioselective Diels–Alder reaction of anthracene.

ChemInform Abstract: Nanoporous Solid Acid Catalyst for the Diels-Alder Reaction of 1,3-Dienes with Acrylates.

ChemInform ◽  
2010 ◽  
Vol 33 (28) ◽  
pp. no-no
Author(s):  
Makoto Onaka ◽  
Naoki Hashimoto ◽  
Ryota Yamasaki ◽  
Yasuyoshi Kitabata
Keyword(s):  
Solid Acid ◽  
Solid Acid Catalyst ◽  
Acid Catalyst ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction
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