Cobalt-catalyzed cycloisomerization of 1,6-enynes and allyl propargyl ethers

Organic Letters

Volumn 5, Issue 14, 2003, Pages 2409-2411

  Ajamian, Alain ^a   Gleason, James L ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

1,6 ENYNE; ALKENE DERIVATIVE; ALKYNE DERIVATIVE; COBALT; COBALT DERIVATIVE; CYCLOPENTENE DERIVATIVE; DICOBALT OCTACARBONYL; ETHER; FURAN DERIVATIVE; PHOSPHITE; TRIMETHYL PHOSPHITE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CYCLIZATION; CYCLOISOMERIZATION; ISOMERISM;

EID: 0141743337     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034541f     Document Type: Article

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26. 3 in methanol to remove the acetylenic TMS group allowed 3 to be removed as a volatile component. This allowed 4 to be isolated in pure form in 91% yield. The reaction can be conducted on > 1 mmol scale with ease (see Supporting Information).
27. Although initial studies (ref 2) did not reveal any cyclization of 4 under stoichiometric conditions, subsequent studies have shown that 4 does indeed slowly cyclize to 1 in low yield (20%) under stoichiometric conditions.
28. Malonates similar to 14 possessing an -OTBS group at the propargylic position also fail to give the desired cycloisomerization product.
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