期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 15, 期 38, 页码 9773-9784出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200901292
关键词
cycloisomerization; cyclopropanes; diastereoselectivity; homogeneous catalysis; natural products
We describe in detail a direct, stereoselective synthesis of (-)-cubebol based on it Pt-, Au-, or Cu-catalyzed cycloisomerization in which control of the configuration of the propargylic center is essential for the facial selectivity. In addition, we show that cycloisomerization reactions of enantioenriched propargyl pivalates occur with substantial chirality transfer. We confirm it mechanism by means of cyclization followed by an [1,2]-acyl migration for the Pt- and the Au-catalyzed cycloisomerization. So far, no evidence supports that the Cu-catalyzed cycloisomerization follows the same reaction course.
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