Synthesis of cyclic ethers via the palladium catalyzed intramolecular hydrocarbonation of alkoxyallenes

Tetrahedron Letters

Volumn 40, Issue 9, 1999, Pages 1747-1750

  Kamijo, Shin ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Allenes; Cyclization; Oxygen heterocycles; Palladium catalysts

Indexed keywords

ALLENE DERIVATIVE; ETHER DERIVATIVE; PALLADIUM;

ARTICLE; CATALYSIS; CYCLIZATION; MOLECULAR INTERACTION; SYNTHESIS;

EID: 0033605275     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02681-1     Document Type: Article

References (16)

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15. 2 was added methanesulfonyl chloride (3.0 ml, 40 mmol) and stirred for 30 min at 0 °C. The crude product was obtained after extraction with ether and was purified by silica gel column chromatography to give 1-methanesulfonyl-4-oxa-5,6-heptadiene in 57% yield (for 2 steps). To a suspension of NaH (0.34 g, 60% in mineral oil, 8 mmol) in THF was added malononitrile (1.6 g, 24 mmol) at 0 °C and stirred for 10 min at room temperature, then, DMF was added and stirred for extra 20 min. A solution of the mesylate (1.54 g, 8 mmol) in THF and a catalytic amounts of potassium iodide was introduced to the reaction mixture and stirred for 2 h at 80 °C. The crude product was purified by silica gel column chromatography using n-hexane/ethyl acetate (5/1) to give 3a in 54% yield.
16. 5. Unpublished result. Addition of acetic acid dramatically enhances the cyclization of allenes to afford carbocycles.