Microwave-assisted, regioselective, Petasis olefination of unsymmetrical oxalates. Formation of pyruvate-based enol ethers and enamines

Tetrahedron Letters

Volumn 46, Issue 2, 2005, Pages 297-300

  Cook, Matthew J ^a   Fleming, Declan W ^a   Gallagher, Timothy ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

Enamines; Enol ethers; Olefination; Petasis reagent; Pyruvates

Indexed keywords

ENAMINE; ETHER DERIVATIVE; OXALIC ACID; PYRUVIC ACID;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; MICROWAVE RADIATION; OLEFINATION; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY; THERMODYNAMICS;

EID: 10044229525     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.11.070     Document Type: Article

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25. 7a All novel compounds were fully characterised with the exception of 4a which was highly volatile and proved difficult to isolate free of solvent. As a result, only a solution yield of 4a was determined
26. 3 (66 mol %) as a very mild Lewis acid. This procedure clearly raises issues associated with toxicity and scale up
27. 19 Representive thermal (nonmicrowave-assisted) conditions: tert-butyl-N,N- dimethylamino oxalate 3e (50 mg, 0.265 mmol) and dimethyl titanocene 1 (165 mg, 1.65 mL, 0.795 mmol, 0.48 M in THF/toluene, 3.0 equiv) were heated at 75°C for 24 h. Product 4e was isolated as described above and in a similar yield
28. 2 requires C, 68.21; H, 10.02; N, 6.63. Found: C, 68.02; H, 10.20; N, 6.35