Synthesis of highly substituted pyrrolidines via palladium catalysed formal [2+3] cycloaddition of 5-vinyloxazolidin-2-ones to activated alkenes

Tetrahedron Letters

Volumn 46, Issue 37, 2005, Pages 6261-6264

  Knight, Julian G ^a   Tchabanenko, Kirill ^a   Stoker, Paul A ^a   Harwood, Simon J ^b  

^a NEWCASTLE UNIVERSITY   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

Catalytic; Cycloaddition; Palladium; Pyrrolidine; Synthesis

Indexed keywords

ALKENE; GLYCINE; MALONIC ACID; OXAZOLIDINE DERIVATIVE; PALLADIUM; PYRROLIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CYCLOADDITION; DECARBOXYLATION; DRUG STRUCTURE; ELECTRON; REACTION ANALYSIS; SUBSTITUTION REACTION;

EID: 23744509485     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.07.053     Document Type: Article

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12. 1H NMR spectrum was recorded. The NMR yield was calculated from the relative integrals of the signals from 1,3-dinitrobenzene (δ 9.00, 1H, H-2; δ 8.50, 2H, H-4) and the pyrrolidine product 14. (δ 5.14-4.95, 3H, vinyl-H; δ 4.41, 1H, H-5; δ 3.95, 1H, H-5). In the case of Table 1, entry 4, purification of the product resulted in an isolated yield of 17%, close to the NMR yield of 23%.
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