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- W2138996751 abstract "The thermally induced Pauson-Khand intramolecular cyclization of 1-(3-alkoxy-2-propynyloxy)methylcyclopentenes (2) and 1-(5-alkoxy-4-pentynyl)cyclopentenes (3), derived from chiral secondary alcohols, leads to the tricyclic enones (9) and (10), respectively, in moderate yields and with variable diastereoselectivities. Among the chiral alcohols that we have examined, enynes derived from Oppolzer's 3-(neopentyloxy)isoborneol 4c afford chromatographically-separable diastereomers, and those derived from 10-(methylthio)isoborneol 4d are cyclized with outstanding stereocontrol (up to 12:1 d.r., one of the highest values recorded to date for chiral auxiliary-stereocontrolled intramolecular Pauson-Khand reactions). These results open for the first time a way to the enantioselective synthesis of angular triquinanes in which the tricyclic skeleton is stereoselectively constructed in a single step from a monocyclic enyne without internal stereogenic centers." @default.
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- W2138996751 date "1996-10-01" @default.
- W2138996751 modified "2023-10-16" @default.
- W2138996751 title "Chiral auxiliary-induced stereocontrol in intramolecular Pauson-Khand reactions leading to angular triquinanes" @default.
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- W2138996751 doi "https://doi.org/10.1016/0040-4020(96)00844-7" @default.
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