Palladium-catalyzed diastereoselective coupling of propargylic oxiranes with terminal alkynes.
[reaction: see text] A diastereoselective coupling of propargylic oxiranes with terminal alkynes has been developed with use of a palladium catalyst. The stereochemistries of the resulting 4-alkynyl-substituted 2,3-allenols have been altered depending on the palladium catalyst. An optically active anti-substituted allene was synthesized from the reaction of an enantiomerically enriched propargylic oxirane without loss of chirality.
Yoshida
Masahiro
M
Graduate School of Pharmaceutical Sciences, The University of Tokushima, 1-78-1 Sho-machi, Tokushima 770-8505, Japan. yoshida@ph.tokushima-u.ac.jp
Hayashi
Maiko
M
Shishido
Kozo
K
D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D005027:Ethylene Oxide / Q000737:chemistry*; D015394:Molecular Structure; D009019:Morphinans / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
D000480:Alkynes; D009019:Morphinans; D010165:Palladium; D005027:Ethylene Oxide