Palladium-catalyzed diastereoselective coupling of propargylic oxiranes with terminal alkynes

Organic Letters

Volumn 9, Issue 9, 2007, Pages 1643-1646

  Yoshida, Masahiro ^a   Hayashi, Maiko ^a   Shishido, Kozo ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; ETHYLENE OXIDE; MORPHINAN DERIVATIVE; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

ALKYNES; CATALYSIS; ETHYLENE OXIDE; MOLECULAR STRUCTURE; MORPHINANS; PALLADIUM; STEREOISOMERISM;

EID: 34248375268     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol070224n     Document Type: Article

References (23)

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22. 3 as the palladium catalyst, the production of syn-3aa was decreased (syn-3aa:anti- 3aa = 1:6.5, 91% total yields). The result implies that the palladium(II) species which is partly generated in situ during the coupling process causes the isomerization of the resulting allenes.
23. Recently, Molander et al. reported the racemization of chiral alkenylallenes in the palladium-catalyzed coupling of propargylic phosphates with alkenyl trifluoroborates: Molander, G. A.; Sommers, E. M.; Baker. S. R. J. Org. Chem. 2006, 71, 1563.