Optimization of palladium-catalyzed polyene cyclizations: Suppression of competing hydride transfer from tertiary amines with dabco and an unexpected hydride transfer from 1,4-dioxane

Organic Letters

Volumn 3, Issue 2, 2001, Pages 181-184

  Lau, Stephen Y W ^a   Andersen, Neil G ^a   Keay, Brian A ^a  

^a UNIVERSITY OF CALGARY   (Canada)

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ARTICLE;

EID: 0000020677     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006740u     Document Type: Article

References (48)

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45. 3, EtOH).
46. Non-amine bases such as potassium carbonate completely inhibited the polyene cyclization, and only unreacted starting material 2 or 3 was obtained.
47. To date we have not been able to detect (by NMR) or isolate 2,3-dihydro-[1,4]-dioxine (15) in the reaction mixture. Work is continuing to determine the fate of dioxane in these systems.
48. Dabco: $0.40 per g. PMP: $15.64 per g. Source: Aldrich Handbook of Fine Chemicals and Laboratory Equipment, 2000.