Stereochemically controlled syntheses of some bicyclo[n.3.0]alkane-1-carboxylic acids

1978 ◽  
Vol 56 (1) ◽  
pp. 93-98 ◽  
Author(s):  
E. W. Warnhoff ◽  
W. T. Tai ◽  
Y. C. Toong
Keyword(s):  
Carboxylic Acids ◽  
Alder Reaction ◽  
Diels Alder ◽  
Ring Fusion ◽  
Diels Alder Reaction ◽  
Cyclopentane Ring ◽  
Methods Of Synthesis ◽  
Cis And Trans

Stereospecific methods of synthesis of some cis- and trans-bicyclo[n.3.0]alkane-1-carboxylic acids are described, specifically 5a, 5b, and 11. The cis ring fusion is insured by use of the Diels–Alder reaction, and the trans ring fusion is fixed by the necessity of a cis attachment of an intermediate five-membered cyclic lactamol to the existing cyclopentane ring in 9.

Photochemistry of 2,4-Cyclooctadienone I. In Benzene and Toluene

1973 ◽  
Vol 51 (13) ◽  
pp. 2207-2214 ◽  
Author(s):  
Gordon L. Lange ◽  
Eli Neidert
Keyword(s):  
Singlet State ◽  
Alder Reaction ◽  
Diels Alder ◽  
Reactive Intermediate ◽  
Diels Alder Reaction ◽  
Trans Isomerization ◽  
Dimerization Reaction ◽  
Cis And Trans

Irradiation of 2,4-cyclooctadienone (1) in benzene or toluene is shown to give in >80% yield two head-to-head dimers. The ring fusions are shown to occur at the α,β-positions of the dienone with trans-cis and trans-anti-trans stereochemistry. Both dimers may be epimerized to the same product with cis-anti-cis ring fusions. Evidence is presented to show that the singlet state is responsible for the cis-trans isomerization of 1 to the highly reactive intermediate trans, cis-2,4-cyclooctadienone. This intermediate can dimerize in a thermal 2 + 2 cycloaddition or can be generated at −78° and then trapped by 1,3-dienes in a Diels–Alder reaction. A mechanism for the dimerization reaction is discussed.

endo and exo Ring fusion in the Diels–Alder reaction of 1-(2,4,6-trialkylphenyl-)3-methylphospholes with maleic acid derivatives

Tetrahedron ◽  
2002 ◽  
Vol 58 (49) ◽  
pp. 9801-9808 ◽  
Author(s):  
György Keglevich ◽  
László Nyulászi ◽  
Tungalag Chuluunbaatar ◽  
Bat-Amgalan Namkhainyambuu ◽  
Krisztina Ludányi ◽  
...  
Keyword(s):  
Maleic Acid ◽  
Alder Reaction ◽  
Diels Alder ◽  
Ring Fusion ◽  
Diels Alder Reaction

Asymmetric synthesis of 2-aminonorbornane-2-carboxylic acids by Diels-Alder reaction

1991 ◽  
Vol 2 (12) ◽  
pp. 1295-1304 ◽  
Author(s):  
Carlos Cativiela ◽  
Pilar López ◽  
José A. Mayoral
Keyword(s):  
Asymmetric Synthesis ◽  
Carboxylic Acids ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction

scholarly journals TiCl3 as a New Catalyst for the Imino Diels-Alder Reaction

2006 ◽  
Vol 1 (9) ◽  
pp. 1934578X0600100
Author(s):  
Narayan V. Mayekar ◽  
Sandip K. Nayak ◽  
Subrata Chattopadhyay
Keyword(s):  
Ambient Temperature ◽  
Alder Reaction ◽  
Diels Alder ◽  
Trans Isomers ◽  
Effective Catalyst ◽  
Diels Alder Reaction ◽  
Cis And Trans Isomers ◽  
Reaction Proceeds ◽  
Cis And Trans

Titanium(III) chloride was found to be an effective catalyst for the imino Diels-Alder reaction between an imine (generated in situ) and an activated alkene in acetonitrile at ambient temperature. The reaction proceeds smoothly to afford the corresponding adduct as a mixture of chromatographically separable cis- and trans isomers in moderate to good yields.

New synthetic approach to substituted isoindolo[2,1-a]quinoline carboxylic acids via intramolecular Diels–Alder reaction of 4-(N-furyl-2)-4-arylaminobutenes-1 with maleic anhydride

Tetrahedron ◽  
2005 ◽  
Vol 61 (16) ◽  
pp. 4099-4113 ◽  
Author(s):  
Fedor I. Zubkov ◽  
Ekaterina V. Boltukhina ◽  
Konstantin F. Turchin ◽  
Roman S. Borisov ◽  
Alexey V. Varlamov
Keyword(s):  
Maleic Anhydride ◽  
Carboxylic Acids ◽  
Alder Reaction ◽  
Diels Alder ◽  
Synthetic Approach ◽  
Diels Alder Reaction
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