Synthesis of Optically Active Tetrahydro-3-benzazepine-2-carboxylic Acid Derivatives via the Ring Expansion Reaction of Isoquinolines and Enzymatic Resolution

Heterocycles ◽  
2004 ◽  
Vol 63 (1) ◽  
pp. 17 ◽  
Author(s):  
Tatsuo Nagasaka ◽  
Yuji Koseki ◽  
Hidefumi Ozawa ◽  
Katsuaki Kitahara ◽  
Ichiro Kato ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Ring Expansion ◽  
Optically Active ◽  
Enzymatic Resolution ◽  
Ring Expansion Reaction

The resolution of endo-bicyclo[3.3.1]non-6-en-3-carboxylic acid and its conversion to optically active adamantanones

1977 ◽  
Vol 18 (20) ◽  
pp. 1761-1764 ◽  
Author(s):  
H. Numan ◽  
C.B. Troostwijk ◽  
J.H. Wieringa ◽  
Hans Wynberg
Keyword(s):  
Carboxylic Acid ◽  
Optically Active

Unusual Ring-Expansion Reaction of Polyfluorinated Norbornenoxetanes

Synthesis ◽  
2007 ◽  
Vol 2007 (9) ◽  
pp. 1349-1354 ◽  
Author(s):  
Viacheslav Petrov ◽  
Will Marshall
Keyword(s):  
Ring Expansion ◽  
Ring Expansion Reaction

Enzymatic resolution of (±)-5-phenyl-4,5-dihydroisoxazole-3-carboxylic acid ethyl ester and its transformations into polyfunctionalised amino acids and dipeptides

2009 ◽  
Vol 20 (16) ◽  
pp. 1940-1947 ◽  
Author(s):  
Giuseppe Cremonesi ◽  
Piero Dalla Croce ◽  
Alessandra Forni ◽  
Maddalena Gallanti ◽  
Raffaella Gandolfi ◽  
...  
Keyword(s):  
Amino Acids ◽  
Carboxylic Acid ◽  
Ethyl Ester ◽  
Acid Ethyl Ester ◽  
Enzymatic Resolution

Synthesis of Optically Active Hydroxyalkyl Cycloheptatrienes: A Key Step in the Total Synthesis of 6,11-Methylene-LXB4

Synlett ◽  
2020 ◽  
Vol 32 (01) ◽  
pp. 45-50
Author(s):  
Udo Nubbemeyer ◽  
Analuisa Nava ◽  
Lukas Trippe ◽  
Andrea Frank ◽  
Lars Andernach ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Total Synthesis ◽  
Structure Elucidation ◽  
Butyl Ester ◽  
Optically Active ◽  
Chiral Hplc ◽  
Reaction Conditions ◽  
Acid Product ◽  
Tert Butyl ◽  
Nabh4 Reduction

AbstractStarting from methyl cycloheptatrienyl-1-carboxylate, 6-acylation was successfully achieved employing glutaryl chloride in the presence of AlCl3 under controlled reaction conditions to furnish keto carboxylic acid product. After protection of this keto carboxylic acid as tert-butyl ester, reagent-controlled enantioselective reductions delivered configuration-defined methyl-6-hydroxylalkyl cycloheptatriene-1-carboxylates with up to 80% ee. Whereas simple NaBH4 reduction of the keto carboxylic acid and subsequent lactonization afforded a methyl-6-tetrahydropyranonyl cycloheptatriene-1-carboxylate. Resolution using chiral HPLC delivered the product enantiomers with up to >99% ee Finally, ECD analyses enabled structure elucidation. The products are used as key intermediates in enantioselective 6,11-methylene-lipoxin B4 syntheses.

Synthesis and Ring Cyclization - Expansion - Contraction Reactions of Some New 2,2-Disubstituted Indan-1,3-diones and Related Compounds

2006 ◽  
Vol 59 (1) ◽  
pp. 59 ◽  
Author(s):  
Craig J. Roxburgh ◽  
Lee Banting
Keyword(s):  
Catalytic Hydrogenation ◽  
Pyridine Ring ◽  
Functional Group ◽  
Chemical Properties ◽  
Ring Expansion ◽  
Ring Structure ◽  
Side Reactions ◽  
The Third ◽  
Ring Expansion Reaction ◽  
Related Compounds

We have found that the hydrochloride of 2-phenyl-2-[2-(2-piperidyl)ethyl]-4,5,6,7-tetrahydroindan-1,3-dione 1 possesses marked analgesic activity (100% inhibition referenced to codeine) and report, as part of an extensive synthetic program, the synthesis of 38 new and structurally related compounds. Selective catalytic hydrogenation of the pyridine ring of 2-phenyl-2-[2-(2-pyridyl)ethyl]-indan-1,3-dione 2 yields the nine-membered nitrogen-containing heterocycle 6 by a novel ring cyclization–expansion reaction. The structural and functional group parameters required for this novel ring-expansion reaction have been extensively and thoroughly investigated through the synthesis of a series of structurally related compounds; principally by modification, substitution, and replacement of the various functionality contained within 2. In addition, we report the synthesis of a series of new 2-methyl-2-(ω-N-phthalimidoalkyl)-indan-1,3-diones 41, 45, and 53, two of which, like the parent 2-phenyl substituted indan-1,3-dione 2, also undergo a novel ring cyclization–expansion reaction to yield eight- and nine-membered nitrogen-containing rings. However, in these cases, further transannular reactions occur to produce the new 5,5- and 5,6-ring-fused nitrogen-containing heterocycles 44, 48 and 51, 52. Hydrazinolysis of the third, 2-methyl-2-(4-N-phthalimidobutyl)-indan-1,3-dione yields the new azepine-containing ring structure 56 by direct cyclization. Furthermore, some interesting and unexpected chemical properties of the final compounds, which include selective and non-selective pyridine-ring hydrogenations and a few unexpected side reactions, are described.

Sign in / Sign up

Export Citation Format

Share Document