Four-step one-pot catalytic asymmetric synthesis of multisubstituted tricyclic compounds: Lipase-catalyzed dynamic kinetic resolution followed by an intramolecular Diels–Alder reaction

Synlett ◽  
2021 ◽  
Author(s):  
Izuru Tsuchimochi ◽  
Shuhei Hori ◽  
Yasuo Takeuchi ◽  
Masahiro Egi ◽  
Tomo-o Satoh ◽  
...  
Keyword(s):  
Hydroxy Group ◽  
Kinetic Resolution ◽  
Alder Reaction ◽  
Diels Alder ◽  
One Pot ◽  
Diels Alder Reaction ◽  
Tricyclic Compounds ◽  
High Yields ◽  
Group Migration ◽  
Oxovanadium Compounds

Starting from readily available tertiary alcohols, four different reactions (i.e., a 1,3-migration of a hydroxy group, kinetic resolution, racemization, and an intramolecular Diels–Alder reaction) took place under the co-catalysis of lipase and oxovanadium compounds in a one-pot process to produce multisubstituted tricyclic carbon frameworks in high yields and high enantioselectivities. The key to the success of this process was the discovery that the silyl group attached to the terminal carbon of the vinyl moiety completely controls the direction of hydroxy group migration.

scholarly journals T3P- A Novel Catalyst for Aza-Diels-Alder Reaction: One-Pot Synthesis of Pyrano[3,2-c]quinolines and furano[3,2-c]quinolines

2011 ◽  
Vol 8 (s1) ◽  
pp. S420-S424 ◽  
Author(s):  
T. S. R. Prasanna ◽  
K. Mohana Raju
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
One Pot ◽  
Efficient Catalyst ◽  
One Pot Synthesis ◽  
Diels Alder Reaction ◽  
Short Period ◽  
High Yields ◽  
Novel Catalyst

T3P was found to be an efficient catalyst for the Aza-Diels–Alder reactions of aldimines with dihydropyran or dihydrofuran to afford the corresponding pyrano-and furo [3,2-c]quinolines in high yields with high diastereoselectivity in a short period of time.

scholarly journals Efficient synthesis of polyfunctionalized carbazoles and pyrrolo[3,4-c]carbazoles via domino Diels–Alder reaction

2021 ◽  
Vol 17 ◽  
pp. 2425-2432
Author(s):  
Ren-Jie Fang ◽  
Chen Yan ◽  
Jing Sun ◽  
Ying Han ◽  
Chao-Guo Yan
Keyword(s):  
Room Temperature ◽  
Alder Reaction ◽  
Diels Alder ◽  
Efficient Synthesis ◽  
One Pot ◽  
Diels Alder Reaction ◽  
Acid Catalyzed ◽  
The One ◽  
High Yields ◽  
Ddq Oxidation

The p-TsOH-catalyzed Diels–Alder reaction of 3-(indol-3-yl)maleimides with chalcone in toluene at 60 °C afforded two diastereoisomers of tetrahydropyrrolo[3,4-c]carbazoles, which can be dehydrogenated by DDQ oxidation in acetonitrile at room temperature to give the aromatized pyrrolo[3,4-c]carbazoles in high yields. On the other hand, the one-pot reaction of 3-(indol-3-yl)-1,3-diphenylpropan-1-ones with chalcones or benzylideneacetone in acetonitrile in the presence of p-TsOH and DDQ resulted in polyfunctionalized carbazoles in satisfactory yields. The reaction mechanism included the DDQ oxidative dehydrogenation of 3-(indol-3-yl)-1,3-diphenylpropan-1-ones to the corresponding 3-vinylindoles, their acid-catalyzed Diels–Alder reaction and sequential aromatization process.

scholarly journals Efficient synthesis of polyfunctionalized carbazoles and pyrrolo[3,4-c]carbazoles via domino Diels-Alder reaction

2021 ◽  
Author(s):  
Ren-Jie Fang ◽  
Chen Yan ◽  
Jing Sun ◽  
Ying Han ◽  
Chao-Guo Yan
Keyword(s):  
Room Temperature ◽  
Alder Reaction ◽  
Diels Alder ◽  
Efficient Synthesis ◽  
One Pot ◽  
Diels Alder Reaction ◽  
Acid Catalyzed ◽  
The One ◽  
High Yields ◽  
Ddq Oxidation

p-TsOH catalyzed Diels-Alder reaction of 3-(indol-3-yl)maleimides with chalcone in toluene at 60 oC afforded two diastereoisomers of tetrahydropyrrolo[3,4-c]carbazoles, which can be dehydrogenated by DDQ oxidation in acetonitrile at room temperature to give the aromatized pyrrolo[3,4-c]carbazoles in high yields. On the other hand, the one-pot reaction of 3-(indol-3-yl)-1,3-diphenylpropan-1-ones with chalcones in acetonitrile in the presence of p-TsOH and DDQ resulted in polyfunctionalized carbazoles in satisfactory yields. The reaction mechanism included DDQ oxidative dehydrogenation of 3-(indol-3-yl)-1,3-diphenylpropan-1-ones to the corresponding 3-vinylindoles, its acid-catalyzed Diels-Alder reaction and sequential aromatization process.

l-Proline-Catalysed One-Pot aza-Diels–Alder Reaction in Water: Regioselective Synthesis of Spiro(isoxazolo[5,4-b]pyridine-5,5′-pyrimidine) Derivatives

Synlett ◽  
2018 ◽  
Vol 29 (09) ◽  
pp. 1195-1198 ◽  
Author(s):  
Yuvaraj Dommaraju ◽  
Somadrita Borthakur ◽  
Dipak Prajapati
Keyword(s):  
Hydroxylamine Hydrochloride ◽  
Aromatic Aldehydes ◽  
Good Alternative ◽  
Alder Reaction ◽  
Diels Alder ◽  
Pyrimidine Derivatives ◽  
One Pot ◽  
Diels Alder Reaction ◽  
Spiro Derivatives ◽  
High Yields

A simple and efficient l-proline-catalysed synthesis of spiro(isoxazolo[5,4-b]pyridine-5,5′-pyrimidine) derivatives in water has been accomplished through a pseudo five-component one-pot domino aza-Diels–Alder reaction involving 3-amino crotanonitrile, hydroxylamine hydrochloride, aromatic aldehydes and barbituric acids. The main advantages of the present method are mild reaction conditions, modest purification process involving no chromatographic techniques and high yields. The protocol is a good alternative to prepare spiro derivatives with readily available starting materials, which makes the method highly attractive.

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