期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 72, 期 7, 页码 2651-2654出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo062594f
关键词
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The mechanism of the intramolecular Pt(II)-catalyzed Rautenstrauch cyclopropanation and the stereochemical implications have been investigated by computational methods. The reaction takes place through a cyclopropanation step preceding the cleavage of the C-O bond, thus ensuring the transfer of chiral information from the stereogenic propargylic center. Our results agree with experimental findings and account for the origin of the substrate-dependent selectivity on the basis of subtle electronic effects and steric interactions in the cyclopropanation transition-state structure.
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